3-aminoimidazo [1,2-a] pyridine derivatives as sglt inhibitors

ABSTRACT

Novel compounds of the formula I, in which X, Y, R, R′, R 1 , R 1′ , R 1″ , R 2 , R 2′ , R 2″ , R 3 , R 3′ , R 4 , R 4′  and n have the meanings indicated in Patent Claim  1 , are suitable as antidiabetics

The invention relates to compounds of the formula I

in which

-   R, R′ each, independently of one another, denote A, OA, Hal, NO₂ or    COOA,-   R¹, R^(1′) each, independently of one another, denote H, A, F, Cl,    NH₂, OH, CN or COOH,-   R^(1″) denotes H or NH₂,-   R², R^(2′) each, independently of one another, denote H, Hal, A, OH,    OA, CN, NO₂, NR⁴R^(4′), CH₂NR⁴R^(4′), O(CH₂)_(m)NR⁴R^(4′),    O(CH₂)_(m)OR⁴, NH(CH₂)_(m)NR⁴R^(4′), O(C═O)(CH₂)_(m)NR⁴R^(4′),    NH(C═O)(CH₂)_(m)NR⁴R^(4′), CH₂O(CH₂)_(m)NR⁴R^(4′), CH₂OR⁴,    (CH₂)_(m)COOR⁴, OSO₂A, OHet, O(CH₂)_(m)CONR⁴R^(4′), O(CH₂)_(m)Ar,    O(CH₂)_(m)CH(OH)(CH₂)_(m)OH or OSO₂NR⁴R^(4′),-   R² and R^(2′) together also denote —CH═CH—CH═CH—,-   R^(2″) denotes H, A, Hal, OH or OA,-   R³, R^(3′) each, independently of one another, denote H, A, Hal, NO₂    or COOA,-   R⁴, R^(4′) each, independently of one another, denote H or A,-   X, Y each, independently of one another, denote O, NH, CH₂ or are    absent,-   A denotes unbranched or branched alkyl having 1-10 C atoms, in which    1-7 H atoms may be replaced by F, or cycloalkyl having 3-7 C atoms,-   Het denotes a monocyclic saturated heterocycle having 1 to 2 N, O    and/or S atoms, which may be mono- or disubstituted by A, Hal, OA,    OH and/or ═O (carbonyl oxygen),-   Ar denotes phenyl which is unsubstituted or mono-, di-, tri- or    tetra-substituted by A, Hal, OA and/or OH,-   Hal denotes F, Cl, Br or I,-   m denotes 1, 2 or 3,-   n denotes 0, 1 or 2,    and pharmaceutically usable derivatives, solvates, salts and    stereoisomers thereof, including mixtures thereof in all ratios.

The invention had the object of finding novel compounds having valuableproperties, in particular those which can be used for the preparation ofmedicaments.

It has been found that the compounds of the formula I and salts thereofhave very valuable pharmacological properties while being welltolerated. They exhibit SGLT1- and SGLT2-(sodium dependent glucoseco-transporter) inhibiting properties and can therefore be employed forcombating and preventing type 1 and type 2 diabetes.

The absorption of glucose in the brush border of the small intestine andthe proximal tubules of the kidney against a concentration gradientoccurs via epithelial sodium-dependent glucose cotransporters (SGLTs).At least two major classes of SGLTs have been described: SGLT1 (forexample Lee W. S. et al. (1994) The high-affinity Na⁺/glucosecotransporter: reevaluation of function and distribution of expression.J. Biol. Chem. 269, 12032-12039) and SGLT2 (for example Mackenzie B. etal. (1994) SAAT1 is a low-affinity Na⁺/glucose cotransporter and not anamino acid transporter. J. Biol. Chem. 269, 22488-22491).

SGLT1 is thought to be important for the absorption of glucose in thegut, whereas SGLT2 is probably primarily responsible for there-absorption of freely filtered glucose in the kidney.

The major change in diabetes mellitus is hyperglycaemia. This is notonly a symptom of the disease, but also a potential pathogenic factorleading to multiple chronic diabetic micro- and macrovascularcomplications and an impairment of insulin secretion and sensitivity(Klein R. (1995), Hyperglycemia and microvascular and macrovasculardisease in diabetes, Diabetes Care 18, 258-268; Rossetti L. (1995),Glucose toxicity: the implications of hyperglycemia in thepathophysiology of diabetes mellitus, Clin. Invest. Med. 18, 255-260).Thus, an important therapeutic aim in the case of the diabetes patientis excusive regulation of the blood glucose levels within the normalrange. In accordance with their described function, inhibition of SGLTsresults in reduced absorption and increased excretion of glucose, and asubsequent dsecrease in blood glucose levels. Thus, suppression of SGLTsmay be a suitable alternative for the treatment of diabetes.

The literature describes a number of classes of substance having an SGLTaction. The model for all these structures was the natural productphlorizin. Aromatic glycoside derivatives are known from WO 2004/052902and WO 2004/052903. Propiophenone glycosides are described in WO0280936, WO 0280935, JP 2000080041 and EP 850948.Glucopyranosyloxybenzylbenzenes are described in WO 0244192, WO 0228872and WO 0168660. Glucopyranosyloxypyrazoles are known from WO 0268440, WO0268439, WO 0236602 and WO 0116147. O-glycoside benzamides are disclosedin WO 0174835 and WO 0174834. C-arylglycosides are described in WO0127128 and US 2002137903. All known structures contain the glucose as avery important structural element. Furthermore, US 2002/132807 disclosesdiaryl sulfide compounds for the treatment of inflammatory and immunediseases. EP 0 953 357 A1 describes in general glycoside compounds asrenal drug carriers, and WO 95/23780 describes4-hydroxyphenoxyheterocycloalkyl compounds as skin lighteners.

The compounds according to the invention have high splitting withrespect to the desired affinity from SGLT₂ to SGLT₁.

The compounds of the formula I are distinguished by favourable actionson glucose metabolism, in particular they lower the blood sugar leveland are suitable for the treatment of type 1 and type 2 diabetes. Thecompounds can therefore be employed alone or in combination with furtherblood sugar-lowering active ingredients (antidiabetics).

The compounds of the formula I are furthermore suitable for theprevention and treatment of late damage in diabetes, such as, forexample, nephropathy, retinopathy, neuropathy and syndrome X, obesity,cardiac infarction, myocardial infarction, peripheral arterial occlusiondiseases, thromboses, arteriosclerosis, inflammation, immune diseases,autoimmune diseases, such as, for example, AIDS, asthma, osteoporosis,cancer, psoriasis, Alzheimer's, schizophrenia and infectious diseases,preferably the treatment of type 1 and type 2 diabetes and for theprevention and treatment 15 of late damage in diabetes, syndrome X andobesity.

The compounds of the formula I can be employed as medicament activeingredients in human and veterinary medicine, in particular for thetreatment and prevention of type 1 and type 2 diabetes.

The invention relates to the compounds of the formula I and saltsthereof and to a process for the preparation of compounds of the formulaI and pharmaceutically usable derivatives, solvates, salts andstereoisomers thereof, characterised in that

a) a compound of the formula II

in which

X, Y, R², R^(2′), R^(2″), R⁴, R^(4′) and n have the meanings indicatedin claim 1,

is reacted with a compound of the formula III

in which

R¹, R^(1′) and R^(1″) have the meanings indicated in Claim 1,

and with a compound of the formula IV

in which

R, R′, R³ and R^(3′) have the meanings indicated in Claim 1,

or

b) a compound of the formula II is reacted with a compound of theformula III and with a compound of the formula V

in which

R, R′, R³ and R^(3′) have the meanings indicated in Claim 1,

and/or

a base or acid of the formula I is converted into one of its salts.

The invention also relates to the optically active forms(stereoisomers), the enantiomers, the racemates, the diastereomers andthe hydrates and solvates of these compounds. The term “solvates of thecompounds” is taken to mean adductions of inert solvent molecules ontothe compounds which form owing to their mutual attractive force. Solvateare, for example, mono- or dihydrates or alcoholates.

The term “pharmaceutically usable derivatives” is taken to mean, forexample, the salts of the compounds according to the invention and alsoso-called prodrug compounds.

The term “prodrug derivatives” is taken to mean compounds of the formulaI which have been modified with, for example, alkyl or acyl groups,sugars or oligopeptides and which are rapidly cleaved in the organism toform the active compounds according to the invention.

These also include biodegradable polymer derivatives of the compoundsaccording to the invention, as described, for example, in Int. J. Pharm.115, 61-67 (1995).

The invention also relates to mixtures of the compounds of the formula Iaccording to the invention, for example mixtures of two diastereomers,for example in the ratio 1:1, 1:2, 1:3, 1:4, 1:5, 1:10, 1:100 or 1:1000.

These are particularly preferably mixtures of stereoisomeric compounds.

The compounds according to the invention may also be in variouspolymorphic forms, for example as amorphous and crystalline polymorphicforms. All polymorphic forms of the compounds according to the inventionbelong within the scope of the invention and are a further aspect of theinvention.

For all radicals which occur more than once, their meanings areindependent of one another.

Above and below, the radicals or parameters X, Y, R, R′, R¹,R^(1′)R^(1″), R², R^(2′), R^(2″), R³, R^(3′), R⁴, R^(4′) and n have themeanings indicated under the formula I, unless expressly indicatedotherwise.

A denotes alkyl, is unbranched (linear) or branched, and has 1, 2, 3, 4,5, 6, 7, 8, 9 or 10 C atoms. A preferably denotes methyl, furthermoreethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl or tert-butyl,furthermore also pentyl, 1-, 2- or 3-methylbutyl, 1,1-, 1,2- or2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1-, 2-, 3- or 4-methylpentyl,1,1-, 1,2-, 1,3-, 2,2-, 2,3- or 3,3-dimethylbutyl, 1- or 2-ethylbutyl,1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, 1,1,2- or1,2,2-trimethylpropyl, further preferably, for example, trifluoromethyl.

A very particularly preferably denotes alkyl having 1, 2, 3, 4, 5 or 6 Catoms, preferably methyl, ethyl, propyl, isopropyl, butyl, isobutyl,sec-butyl, tert-butyl, pentyl, hexyl, trifluoromethyl, pentafluoroethylor 1,1,1-trifluoroethyl.

Cycloalkyl preferably denotes cyclopropyl, cyclobutyl, cyclopentyl,cyclohexyl or cycloheptyl.

X preferably denotes O.

Y is preferably absent.

Ar preferably denotes unsubstituted phenyl, furthermore preferablyphenyl which is mono-, di- or trisubstituted, for example, by A, Hal, OAand/or OH.

Het preferably denotes tetra-hydrofuranyl, tetrahydropyranyl,dioxolanyl, pyrrolidinyl, piperidinyl, morpholinyl or piperazinyl, whichmay also be monosubstituted by ═O (carbonyl oxygen).

R, R′ preferably each, independently of one another, denote methyl,ethyl, propyl, isopropyl or chlorine.

R¹ preferably denotes H, A, F, Cl, NH₂, OH, CN or COOH; R^(1′)preferably denotes H, furthermore also F; R^(1″) preferably denotes H,furthermore NH₂.

R², R^(2′) preferably each, independently of one another, denote H, Hal,A, OH, OA, CN, NO₂, NH₂, NHCH₃, N(CH₃)₂, CH₂NH₂, CH₂NHCH₃, CH₂NH(CH₃)₂,O(CH₂)₂NH₂, O(CH₂)₂NHCH₃, O(CH₂)₂N(CH₃)₂, OCH₂NH₂, OCH₂NHCH₃,OCH₂N(CH₃)₂, O(CH₂)₂OH, O(CH₂)₂OCH₃, OCH₂OH, OCH₂OCH₃, NH(CH₂)₂NH₂,NH(CH₂)₂NHCH₃, NH(CH₂)₂N(CH₃)₂, NHCH₂NH₂, NHCH₂NHCH₃, NHCH₂N(CH₃)₂,O(C═O)(CH₂)₂NH₂, O(C═O)(CH₂)₂NHCH₃, O(C═O)(CH₂)₂N(CH₃)₂, O(C═O)CH₂NH₂,O(C═O)CH₂NHCH₃, O(C═O)CH₂N(CH₃)₂, NH(C═O)(CH₂)₂NH₂, NH(C═O)(CH₂)₂NHCH₃,NH(C═O)(CH₂)₂N(CH₃)₂, NH(C═O)CH₂NH₂, NH(C═O)CH₂NHCH₃, NH(C═O)CH₂N(CH₃)₂,CH₂O(CH₂)₂NH₂, CH₂O(CH₂)₂NHCH₃, CH₂O(CH₂)₂N(CH₃)₂, CH₂OCH₂NH₂,CH₂OCH₂NHCH₃, CH₂OCH₂N(CH₃)₂, CH₂OH, CH₂OCH₃, COOCH₃, COOH, CH₂COOCH₃,OSO₂CH₃, tetrahydropyran-2-yloxy, tetrahydropyran-2-yloxy, OCH₂CONH₂,benzyloxy, OCH₂CH(OH)CH₂OH, OSO₂N(CH₃)₂ or OSO₂NH₂.

R³, R^(3′) preferably each, independently of one another, denote H,methyl, fluorine, NO₂ or COOCH₃.

R⁴, R^(4′) preferably each, independently of one another, denote H orCH₃.

Hal preferably denotes F, Cl or Br, but also I.

m preferably denotes 1 or 2; n preferably denotes 0 or 1.

The compounds of the formula I can have one or more centres of chiralityand can therefore occur in various stereoisomeric forms. The formula Icovers all these forms.

Accordingly, the invention relates, in particular, to the compounds ofthe formula I in which at least one of the said radicals has one of thepreferred meanings indicated above. Some preferred groups of compoundscan be expressed by the following sub-formulae Ia to Ig, which conformto the formula I and in which the radicals not designated in greaterdetail have the meaning indicated under the formula I, but in which

-   in Ia A denotes unbranched or branched alkyl having 1, 2, 3, 4, 5 or    6 C atoms, in which 1-5 H atoms may be replaced by F;-   in Ib R¹ denotes H, A, F, Cl, NH₂, OH, CN or COOH,    -   R¹ denotes H;-   in Ic R⁴, R^(4′) each, independently of one another, denote H or    CH₃;-   in Id Het denotes tetrahydrofuranyl, tetrahydropyranyl, dioxolanyl,    pyrrolidinyl, piperidinyl, morpholinyl or piperazinyl, each of which    may also be monosubstituted by ═O (carbonyl oxygen);-   in Ie Ar denotes phenyl;-   in If X denotes O;-   in Ig Y is absent;

and pharmaceutically usable derivatives, solvates, salts andstereoisomers thereof, including mixtures thereof in all ratios.

Preference is furthermore given to compounds according to Claim 1 of theformula Ia

in which

-   R, R′ each, independently of one another, denote A, OA, Hal, NO₂ or    COOA,-   R¹, R^(1′) each, independently of one another, denote H, A, F, Cl,    NH₂, OH, CN or COOA,-   R^(1″) denotes H or NH₂,-   R², R^(2′) each, independently of one another, denote H, Hal, A, OH,    OA, CN, NO₂, NR⁴R^(4′), CH₂NR⁴R^(4′), O(CH₂)_(m)NR⁴R^(4′),    O(CH₂)_(m)OR⁴, NH(CH₂)_(m)NR⁴R^(4′), O(C═O)(CH₂)_(m)NR⁴R^(4′),    NH(C═O)(CH₂)_(m)NR⁴R^(4′), CH₂O(CH₂)_(m)NR⁴R^(4′), CH₂OR⁴,    (CH₂)_(m)COOR⁴, OSO₂A, OHet, O(CH₂)_(m)CONR⁴R^(4′), O(CH₂)_(m)Ar,    O(CH₂)_(m)CH(OH)(CH₂)_(m)OH or OSO₂NR⁴R^(4′),-   R² and R^(2′) together also denote —CH═CH—CH═CH—,-   R^(2″) denotes H, A, Hal, OH or OA,-   R³, R^(3′) each, independently of one another, denote H, A, Hal, NO₂    or COOA,-   R⁴, R^(4′), each, independently of one another, denote H or A,-   A denotes unbranched or branched alkyl having 1, 2, 3, 4, 5 or 6 C    atoms, in which 1-5 H atoms may be replaced by F,-   Het denotes tetrahydrofuranyl, tetrahydropyranyl, dioxolanyl,    pyrrolidinyl, piperidinyl, morpholinyl or piperazinyl, each of which    may also be monosubstituted by ═O (carbonyl oxygen),-   Ar denotes phenyl,-   Hal denotes F, Cl, Br or I,-   m denotes 1, 2 or 3,-   n denotes 0, 1 or 2,

and pharmaceutically usable derivatives, solvates, salts andstereoisomers thereof, including mixtures thereof in all ratios.

The compounds of the formula I and also the starting materials for thepreparation thereof are, in addition, prepared by methods known per se,as described in the literature (for example in the standard works, suchas Houben-Weyl, Methoden der organischen Chemie [Methods of OrganicChemistry], Georg-Thieme-Verlag, Stuttgart), to be precise underreaction conditions which are known and suitable for the said reactions.Use can also be made here of variants which are known per se, but arenot mentioned here in greater detail.

If desired, the starting materials can also be formed in situ so thatthey are not isolated from the reaction mixture, but instead areimmediately converted further into the compounds of the formula I.

The starting compounds of the formulae II, III, IV and V are generallyknown. If they are novel, they can, however, be prepared by methodsknown per se.

Compounds of the formula I can preferably be obtained by reactingcompounds of the formula II with compounds of the formula III.

The reaction is generally carried out in an inert solvent, in thepresence of an activating agent, preferably perchloric acid.

Depending on the conditions used, the reaction time is between a fewminutes and 14 days, the reaction temperature is between about 0° and150°, normally between 5° and 90°, particularly preferably between 10°and 70° C.

Examples of suitable inert solvents are hydrocarbons, such as hexane,petroleum ether, benzene, toluene or xylene; chlorinated hydrocarbons,such as trichloroethylene, 1,2-dichloroethane, tetrachloromethane,chloroform or dichloromethane; alcohols, such as methanol, ethanol,isopropanol, n-propanol, n-butanol or tert-butanol; ethers, such asdiethyl ether, diisopropyl ether, tetra-hydrofuran (THF) or dioxane;glycol ethers, such as ethylene glycol monomethyl or monoethyl ether,ethylene glycol dimethyl ether (diglyme); ketones, such as acetone orbutanone; amides, such as acetamide, dimethylacetamide ordimethylformamide (DMF); nitriles, such as acetonitrile; sulfoxides,such as dimethyl sulfoxide (DMSO); carbon disulfide; carboxylic acids,such as formic acid or acetic acid; nitro compounds, such asnitromethane or nitrobenzene; esters, such as ethyl acetate, or mixturesof the said solvents; ethanol is particularly preferred.

Compounds of the formula I can furthermore be obtained by reactingcompounds of the formula II with compounds of the formulae III and V.

The reaction is generally carried out in an inert solvent, in thepresence of a water-binding agent, preferably T3P® (propylphosphonicanhydride). Depending on the conditions used, the reaction time isbetween a few minutes and 14 days, the reaction temperature is betweenabout 0° and 150°, normally between 5° and 90°, particularly preferablybetween 10° and 70° C.

Pharmaceutical Salts and Other Forms

The said compounds of the formula I can be used in their final non-saltform. On the other hand, the present invention also relates to the useof these compounds in the form of their pharmaceutically acceptablesalts, which can be derived from various organic and inorganic acids andbases by procedures known in the art. Pharmaceutically acceptable saltforms of the compounds of the formula I are for the most part preparedby conventional methods. If the compound of the formula I contains acarboxyl group, one of its suitable salts can be formed by reacting thecompound with a suitable base to give the corresponding base-additionsalt. Such bases are, for example, alkali metal hydroxides, includingpotassium hydroxide, sodium hydroxide and lithium hydroxide; alkalineearth metal hydroxides, such as barium hydroxide and calcium hydroxide;alkali metal alkoxides, for example potassium ethoxide and sodiumpropoxide; and various organic bases, such as piperidine, diethanolamineand N-methyl-glutamine. The aluminium salts of the compounds of theformula I are likewise included. In the case of certain compounds of theformula I, acid-addition salts can be formed by treating these compoundswith pharmaceutically acceptable organic and inorganic acids, forexample hydrogen halides, such as hydrogen chloride, hydrogen bromide orhydrogen iodide, other mineral acids and corresponding salts thereof,such as sulfate, nitrate or phosphate and the like, and alkyl- andmonoaryl-sulfonates, such as ethanesulfonate, toluenesulfonate andbenzenesulfonate, and other organic acids and corresponding saltsthereof, such as acetate, trifluoroacetate, tartrate, maleate,succinate, citrate, benzoate, salicylate, ascorbate and the like.Accordingly, pharmaceutically acceptable acid-addition salts of thecompounds of the formula I include the following: acetate, adipate,alginate, arginate, aspartate, benzoate, benzenesulfonate (besylate),bisulfate, bisulfite, bromide, butyrate, camphorate, camphorsulfonate,caprylate, chloride, chlorobenzoate, citrate, cyclopentanepropionate,digluconate, dihydrogenphosphate, dinitrobenzoate, dodecylsulfate,ethanesulfonate, fumarate, galacterate (from mucic acid), galacturonate,glucoheptanoate, gluconate, glutamate, glycerophosphate, hemisuccinate,hemisulfate, heptanoate, hexanoate, hippurate, hydrochloride,hydrobromide, hydroiodide, 2-hydroxyethanesulfonate, iodide,isethionate, isobutyrate, lactate, lactobionate, malate, maleate,malonate, mandelate, metaphosphate, methanesulfonate, methylbenzoate,monohydrogenphosphate, 2-naphthalenesulfonate, nicotinate, nitrate,oxalate, oleate, palmoate, pectinate, persulfate, phenylacetate,3-phenylpropionate, phosphate, phosphonate, phthalate, but this does notrepresent a restriction.

Furthermore, the base salts of the compounds of the formula I includealuminium, ammonium, calcium, copper, iron(III), iron(II), lithium,magnesium, manganese(III), manganese(II), potassium, sodium and zincsalts, but this is not intended to represent a restriction. Of theabove-mentioned salts, preference is given to ammonium; the alkali metalsalts sodium and potassium, and the alkaline earth metal salts calciumand magnesium. Salts of the compounds of the formula I which are derivedfrom pharmaceutically acceptable organic non-toxic bases include saltsof primary, secondary and tertiary amines, substituted amines, alsoincluding naturally occurring substituted amines, cyclic amines, andbasic ion exchanger resins, for example arginine, betaine, caffeine,chloroprocaine, choline, N,N′-dibenzylethylenediamine (benzathine),dicyclohexylamine, diethanolamine, diethylamine, 2-diethylaminoethanol,2-dimethylaminoethanol, ethanolamine, ethylenediamine,N-ethylmorpholine, N-ethylpiperidine, glucamine, glucosamine, histidine,hydrabamine, isopropylamine, lidocaine, lysine, meglumine,N-methyl-D-glucamine, morpholine, piperazine, piperidine, polyaminoresins, procaine, purines, theobromine, triethanolamine, triethylamine,trimethylamine, tripropylamine and tris(hydroxymethyl)methylamine(tromethamine), but this is not intended to represent a restriction.

Compounds of the formula I of the present invention which contain basicnitrogen-containing groups can be quaternised using agents such as(C₁-C₄)alkyl halides, for example methyl, ethyl, isopropyl andtert-butyl chloride, bromide and iodide; di(C₁-C₄)alkyl sulfates, forexample dimethyl, diethyl and diamyl sulfate; (C₁₀-C₁₈)alkyl halides,for example decyl, dodecyl, lauryl, myristyl and stearyl chloride,bromide and iodide; and aryl(C₁-C₄)alkyl halides, for example benzylchloride and phenethyl bromide. Both water- and oil-soluble compounds ofthe formula I can be prepared using such salts.

The above-mentioned pharmaceutical salts which are preferred includeacetate, trifluoroacetate, besylate, citrate, fumarate, gluconate,hemisuccinate, hippurate, hydrochloride, hydrobromide, isethionate,mandelate, meglumine, nitrate, oleate, phosphonate, pivalate, sodiumphosphate, stearate, sulfate, sulfosalicylate, tartrate, thiomalate,tosylate and tromethamine, but this is not intended to represent arestriction.

The acid-addition salts of basic compounds of the formula I are preparedby bringing the free base form into contact with a sufficient amount ofthe desired acid, causing the formation of the salt in a conventionalmanner. The free base can be regenerated by bringing the salt form intocontact with a base and isolating the free base in a conventionalmanner. The free base forms differ in a certain respect from thecorresponding salt forms thereof with respect to certain physicalproperties, such as solubility in polar solvents; for the purposes ofthe invention, however, the salts otherwise correspond to the respectivefree base forms thereof.

As mentioned, the pharmaceutically acceptable base-addition salts of thecompounds of the formula I are formed with metals or amines, such asalkali metals and alkaline earth metals or organic amines. Preferredmetals are sodium, potassium, magnesium and calcium. Preferred organicamines are N,N′-dibenzylethylenediamine, chloroprocaine, choline,diethanolamine, ethylenediamine, N-methyl-D-glucamine and procaine.

The base-addition salts of acidic compounds of the formula I areprepared by bringing the free acid form into contact with a sufficientamount of the desired base, causing the formation of the salt in aconventional manner. The free acid can be regenerated by bringing thesalt form into contact with an acid and isolating the free acid in aconventional manner. The free acid forms differ in a certain respectfrom the corresponding salt forms thereof with respect to certainphysical properties, such as solubility in polar solvents; for thepurposes of the invention, however, the salts otherwise correspond tothe respective free acid forms thereof.

If a compound of the formula I contains more than one group which iscapable of forming pharmaceutically acceptable salts of this type, theformula I also encompasses multiple salts. Typical multiple salt formsinclude, for example, bitartrate, diacetate, difumarate, dimeglumine,diphosphate, disodium and trihydrochloride, but this is not intended torepresent a restriction.

With regard to that stated above, it can be seen that the term“pharmaceutically acceptable salt” in the present connection is taken tomean an active ingredient which comprises a compound of the formula I inthe form of one of its salts, in particular if this salt form impartsimproved pharmacokinetic properties on the active ingredient comparedwith the free form of the active ingredient or any other salt form ofthe active ingredient used earlier. The pharmaceutically acceptable saltform of the active ingredient can also provide this active ingredientfor the first time with a desired pharmacokinetic property which it didnot have earlier and can even have a positive influence on thepharmacodynamics of this active ingredient with respect to itstherapeutic efficacy in the body.

Owing to their molecular structure, compounds of the formula I accordingto the invention can be chiral and can accordingly occur in variousenantiomeric forms. They can therefore exist in racemic or in opticallyactive form.

Since the pharmaceutical activity of the racemates or stereoisomers ofthe compounds according to the invention may differ, it may be desirableto use the enantiomers. In these cases, the end product or even theintermediates can be separated into enantiomeric compounds by chemicalor physical measures known to the person skilled in the art or evenemployed as such in the synthesis.

In the case of racemic amines, diastereomers are formed from the mixtureby reaction with an optically active resolving agent. Examples ofsuitable resolving agents are optically active acids, such as the R andS forms of tartaric acid, diacetyltartaric acid, dibenzoyltartaric acid,mandelic acid, malic acid, lactic acid, suitably N-protected amino acids(for example N-benzoylproline or N-benzenesulfonylproline), or thevarious optically active camphorsulfonic acids. Also advantageous ischromatographic enantiomer resolution with the aid of an opticallyactive resolving agent (for example dinitrobenzoylphenylglycine,cellulose triacetate or other derivatives of carbohydrates or chirallyderivatised methacrylate polymers immobilised on silica gel). Suitableeluents for this purpose are aqueous or alcoholic solvent mixtures, suchas, for example, hexane/isopropanol/acetonitrile, for example in theratio 82:15:3.

The invention furthermore relates to the use of the compounds of theformula I and/or physiologically acceptable salts thereof for thepreparation of a medicament (pharmaceutical composition), in particularby non-chemical methods. In this case, they can be converted into asuitable dosage form together with at least one solid, liquid and/orsemi-liquid excipient or adjuvant and optionally in combination with oneor more further active ingredients.

The invention furthermore relates to medicaments comprising at least onecompound of the formula I and/or pharmaceutically usable derivatives,solvates, salts and stereoisomers thereof, including mixtures thereof inall ratios, and optionally excipients and/or adjuvants.

These compositions can be used as medicaments in human or veterinarymedicine.

Pharmaceutical formulations can be administered in the form of dosageunits which comprise a predetermined amount of active ingredient perdosage unit. Such a unit can comprise, for example, 0.5 mg to 1 g,preferably 1 mg to 700 mg, particularly preferably 5 mg to 100 mg, of acompound according to the invention, depending on the disease conditiontreated, the method of administration and the age, weight and conditionof the patient, or pharmaceutical formulations can be administered inthe form of dosage units which comprise a predetermined amount of activeingredient per dosage unit. Preferred dosage unit formulations are thosewhich comprise a daily dose or part-dose, as indicated above, or acorresponding fraction thereof of an active ingredient. Furthermore,pharmaceutical formulations of this type can be prepared using a processwhich is generally known in the pharmaceutical art.

Pharmaceutical formulations can be adapted for administration via anydesired suitable method, for example by oral (including buccal orsublingual), rectal, nasal, topical (including buccal, sublingual ortransdermal), vaginal or parenteral (including subcutaneous,intramuscular, intravenous or intradermal) methods. Such formulationscan be prepared using all processes known in the pharmaceutical art by,for example, combining the active ingredient with the excipient(s) oradjuvant(s).

Pharmaceutical formulations adapted for oral administration can beadministered as separate units, such as, for example, capsules ortablets; powders or granules; solutions or suspensions in aqueous ornon-aqueous liquids; edible foams or foam foods; or oil-in-water liquidemulsions or water-in-oil liquid emulsions.

Thus, for example, in the case of oral administration in the form of atablet or capsule, the active-ingredient component can be combined withan oral, non-toxic and pharmaceutically acceptable inert excipient, suchas, for example, ethanol, glycerol, water and the like. Powders areprepared by comminuting the compound to a suitable fine size and mixingit with a pharmaceutical excipient comminuted in a similar manner, suchas, for example, an edible carbohydrate, such as, for example, starch ormannitol. A flavour, preservative, dispersant and dye may likewise bepresent.

Capsules are produced by preparing a powder mixture as described aboveand filling shaped gelatine shells therewith. Glidants and lubricants,such as, for example, highly disperse silicic acid, talc, magnesiumstearate, calcium stearate or polyethylene glycol in solid form, can beadded to the powder mixture before the filling operation. A disintegrantor solubiliser, such as, for example, agar-agar, calcium carbonate orsodium carbonate, may likewise be added in order to improve theavailability of the medicament after the capsule has been taken.

In addition, if desired or necessary, suitable binders, lubricants anddisintegrants as well as dyes can likewise be incorporated into themixture. Suitable binders include starch, gelatine, natural sugars, suchas, for example, glucose or beta-lactose, sweeteners made from maize,natural and synthetic rubber, such as, for example, acacia, tragacanthor sodium alginate, carboxymethylcellulose, polyethylene glycol, waxes,and the like. The lubricants used in these dosage forms include sodiumoleate, sodium stearate, magnesium stearate, sodium benzoate, sodiumacetate, sodium chloride and the like. The disintegrants include,without being restricted thereto, starch, methylcellulose, agar,bentonite, xanthan gum and the like. The tablets are formulated by, forexample, preparing a powder mixture, granulating or dry-pressing themixture, adding a lubricant and a disintegrant and pressing the entiremixture to give tablets. A powder mixture is prepared by mixing thecompound comminuted in a suitable manner with a diluent or a base, asdescribed above, and optionally with a binder, such as, for example,carboxymethylcellulose, an alginate, gelatine or polyvinylpyrrolidone, adissolution retardant, such as, for example, paraffin, an absorptionaccelerator, such as, for example, a quaternary salt, and/or anabsorbant, such as, for example, bentonite, kaolin or dicalciumphosphate. The powder mixture can be granulated by wetting it with abinder, such as, for example, syrup, starch paste, acadia mucilage orsolutions of cellulose or polymer materials and pressing it through asieve. As an alternative to granulation, the powder mixture can be runthrough a tabletting machine, giving lumps of non-uniform shape whichare broken up to form granules. The granules can be lubricated byaddition of stearic acid, a stearate salt, talc or mineral oil in orderto prevent sticking to the tablet casting moulds. The lubricated mixtureis then pressed to give tablets. The active ingredients can also becombined with a free-flowing inert excipient and then pressed directlyto give tablets without carrying out the granulation or dry-pressingsteps. A transparent or opaque protective layer consisting of a shellacsealing layer, a layer of sugar or polymer material and a gloss layer ofwax may be present. Dyes can be added to these coatings in order to beable to differentiate between different dosage units.

Oral liquids, such as, for example, solution, syrups and elixirs, can beprepared in the form of dosage units so that a given quantity comprisesa pre-specified amount of the compounds. Syrups can be prepared bydissolving the compounds in an aqueous solution with a suitable flavour,while elixirs are prepared using a non-toxic alcoholic vehicle.Suspensions can be formulated by dispersion of the compounds in anon-toxic vehicle. Solubilisers and emulsifiers, such as, for example,ethoxylated isostearyl alcohols and polyoxyethylene sorbitol ethers,preservatives, flavour additives, such as, for example, peppermint oilor natural sweeteners or saccharin, or other artificial sweeteners andthe like, can likewise be added.

The dosage unit formulations for oral administration can, if desired, beencapsulated in microcapsules. The formulation can also be prepared insuch a way that the release is extended or retarded, such as, forexample, by coating or embedding of particulate material in polymers,wax and the like.

The compounds of the formula I and salts, solvates and physiologicallyfunctional derivatives thereof and the other active ingredients can alsobe administered in the form of liposome delivery systems, such as, forexample, small unilamellar vesicles, large unilamellar vesicles andmultilamellar vesicles. Liposomes can be formed from variousphospholipids, such as, for example, cholesterol, stearylamine orphosphatidylcholines.

The compounds of the formula I and the salts, solvates andphysiologically functional derivatives thereof and the other activeingredients can also be delivered using monoclonal antibodies asindividual carriers to which the compound molecules are coupled. Thecompounds can also be coupled to soluble polymers as targeted medicamentcarriers. Such polymers may encompass polyvinylpyrrolidone, pyrancopolymer, polyhydroxypropylmethacrylamidophenol,polyhydroxyethylaspartamidophenol or polyethylene oxide polylysine,substituted by palmitoyl radicals. The compounds may furthermore becoupled to a class of biodegradable polymers which are suitable forachieving controlled release of a medicament, for example polylacticacid, poly-epsilon-caprolactone, polyhydroxybutyric acid,polyorthoesters, polyacetals, polydihydroxypyrans, polycyanoacrylatesand crosslinked or amphipathic block copolymers of hydrogels.

Pharmaceutical formulations adapted for transdermal administration canbe administered as independent plasters for extended, close contact withthe epidermis of the recipient. Thus, for example, the active ingredientcan be delivered from the plaster by iontophoresis, as described ingeneral terms in Pharmaceutical Research, 3(6), 318 (1986).

Pharmaceutical compounds adapted for topical administration can beformulated as ointments, creams, suspensions, lotions, powders,solutions, pastes, gels, sprays, aerosols or oils.

For the treatment of the eye or other external tissue, for example mouthand skin, the formulations are preferably applied as topical ointment orcream. In the case of formulation to give an ointment, the activeingredient can be employed either with a paraffinic or a water-misciblecream base. Alternatively, the active ingredient can be formulated togive a cream with an oil-in-water cream base or a water-in-oil base.

Pharmaceutical formulations adapted for topical application to the eyeinclude eye drops, in which the active ingredient is dissolved orsuspended in a suitable carrier, in particular an aqueous solvent.

Pharmaceutical formulations adapted for topical application in the mouthencompass lozenges, pastilles and mouthwashes.

Pharmaceutical formulations adapted for rectal administration can beadministered in the form of suppositories or enemas.

Pharmaceutical formulations adapted for nasal administration in whichthe carrier substance is a solid comprise a coarse powder having aparticle size, for example, in the range 20-500 microns, which isadministered in the manner in which snuff is taken, i.e. by rapidinhalation via the nasal passages from a container containing the powderheld close to the nose. Suitable formulations for administration asnasal spray or nose drops with a liquid as carrier substance encompassactive-ingredient solutions in water or oil.

Pharmaceutical formulations adapted for administration by inhalationencompass finely particulate dusts or mists, which can be generated byvarious types of pressurised dispensers with aerosols, nebulisers orinsufflators.

Pharmaceutical formulations adapted for vaginal administration can beadministered as pessaries, tampons, creams, gels, pastes, foams or sprayformulations.

Pharmaceutical formulations adapted for parenteral administrationinclude aqueous and non-aqueous sterile injection solutions comprisingantioxidants, buffers, bacteriostatics and solutes, by means of whichthe formulation is rendered isotonic with the blood of the recipient tobe treated; and aqueous and non-aqueous sterile suspensions, which maycomprise suspension media and thickeners. The formulations can beadministered in single-dose or multidose containers, for example sealedampoules and vials, and stored in the freeze-dried (lyophilised) state,so that only the addition of the sterile carrier liquid, for examplewater for injection purposes, immediately before use is necessary.

Injection solutions and suspensions prepared in accordance with therecipe can be prepared from sterile powders, granules and tablets.

It goes without saying that, in addition to the above particularlymentioned constituents, the formulations may also comprise other agentsusual in the art with respect to the particular type of formulation;thus, for example, formulations which are suitable for oraladministration may comprise flavours.

A therapeutically effective amount of a compound of the formula I and ofthe other active ingredient depends on a number of factors, including,for example, the age and weight of the animal, the precise diseasecondition which requires treatment, and its severity, the nature of theformulation and the method of administration, and is ultimatelydetermined by the treating doctor or vet. However, an effective amountof a compound is generally in the range from 0.1 to 100 mg/kg of bodyweight of the recipient (mammal) per day and particularly typically inthe range from 1 to 10 mg/kg of body weight per day. Thus, the actualamount per day for an adult mammal weighing 70 kg is usually between 70and 700 mg, where this amount can be administered as an individual doseper day or usually in a series of part-doses (such as, for example, two,three, four, five or six) per day, so that the total daily dose is thesame. An effective amount of a salt or solvate or of a physiologicallyfunctional derivative thereof can be determined as the fraction of theeffective amount of the compound per se.

The invention furthermore relates to the use of compounds of the formulaI, in combination with at least one further medicament activeingredient, preferably for the treatment of type 1 and type 2 diabetes,in particular for lowering blood sugar.

Suitable further active ingredients for the combination preparationsare:

All antidiabetics mentioned in the Rote Liste [Red List] 2001, Chapter12. They can be combined with the compounds of the formula I accordingto the invention, in particular in order to enhance the actionsynergistically.

The active-ingredient combination can be administered either byadministration of the active ingredients to the patient or separately inthe form of combination preparations which comprise a plurality ofactive ingredients in a single pharmaceutical composition. Most of theactive ingredients listed below are disclosed in USP Dictionary of USANand International Drug Names, US Pharmacopeia, Rockville 2001.

Antidiabetics include insulin and insulin derivatives, such as, forexample, Lantus® (see www.lantus.com) or HMR 1964, fast-acting insulins(see U.S. Pat. No. 6,221,633), GLP-1 derivatives, such as, for example,those disclosed by Novo Nordisk A/S in WO 98/08871, and orally effectivehypoglycaemic active ingredients.

The orally effective hypoglycaemic active ingredients preferably includesulfonylureas, biguanidines, meglitinides, oxadiazolidinediones,thiazolidinediones, glucosidase inhibitors, glucagon antagonists, GLP-1agonists, calcium channel openers, such as, for example, those disclosedby Novo Nordisk A/S in WO 97/26265 and WO 99/03861, insulin sensitisers,inhibitors of liver enzymes which are involved in the stimulation ofgluconeogenesis and/or glycogenolysis, glucose uptake modulators,compounds which modify fat metabolism, such as antihyperlipidaemicactive ingredients and antilipidaemic active ingredients, compoundswhich reduce the intake of foods, PPAR and PXR agonists, and activeingredients which act on the ATP-dependent potassium channel of the betacells.

In an embodiment of the invention, the compounds of the formula I areadministered in combination with an HMGCoA reductase inhibitor, such assimvastatin, fluvastatin, pravastatin, lovastatin, atorvastatin,cerivastatin, rosuvastatin.

In an embodiment of the invention, the compounds of the formula I areadministered in combination with a cholesterol absorption inhibitor,such as, for example, ezetimibe, tiqueside, pamaqueside.

In an embodiment of the invention, the compounds of the formula I areadministered in combination with a PPAR gamma agonist, such as, forexample, rosiglitazone, pioglitazone, JTT-501, GI 262570.

In an embodiment of the invention, the compounds of the formula I areadministered in combination with PPAR alpha agonist, such as, forexample, GW 9578, GW 7647.

In an embodiment of the invention, the compounds of the formula I areadministered in combination with a mixed PPAR alpha/gamma agonist, suchas, for example, GW 1536, AVE 8042, AVE 8134, AVE 0847, AVE 0897, or asdescribed in WO 00/64888, WO 00/64876, WO 03/20269.

In an embodiment of the invention, the compounds of the formula I areadministered in combination with a fihrate, such as, for example,fenofibrate, clofibrate, bezafibrate.

In an embodiment of the invention, the compounds of the formula I areadministered in combination with an MTP inhibitor, such as, for example,implitapide, BMS-201038, R-103757. In an embodiment of the invention,the compounds of the formula I are administered in combination with bileacid absorption inhibitor (see, for example, U.S. Pat. No. 6,245,744 orU.S. Pat. No. 6,221,897), such as, for example, HMR 1741.

In an embodiment of the invention, the compounds of the formula I areadministered in combination with a CETP inhibitor, such as, for example,JTT-705.

In an embodiment of the invention, the compounds of the formula I areadministered in combination with a polymeric bile acid adsorber, suchas, for example, cholestyramine, colesevelam.

In an embodiment of the invention, the compounds of the formula I areadministered in combination with an LDL receptor inducer (see U.S. Pat.No. 6,342,512), such as, for example, HMR1171, HMR1586.

In an embodiment of the invention, the compounds of the formula I areadministered in combination with an ACAT inhibitor, such as, forexample, avasimibe.

In an embodiment of the invention, the compounds of the formula I areadministered in combination with an antioxidant, such as, for example,OPC-14117.

In an embodiment of the invention, the compounds of the formula I areadministered in combination with a lipoprotein lipase inhibitor, suchas, for example, NO-1886.

In an embodiment of the invention, the compounds of the formula I areadministered in combination with an ATP citrate lyase inhibitor, suchas, for example, SB-204990.

In an embodiment of the invention, the compounds of the formula I areadministered in combination with a squalene synthetase inhibitor, suchas, for example, BMS-188494. In an embodiment of the invention, thecompounds of the formula I are administered in combination with alipoprotein(a) antagonist, such as, for example, CI-1027 or nicotinicacid. In an embodiment of the invention, the compounds of the formula Iare administered in combination with a lipase inhibitor, such as, forexample, orlistat.

In an embodiment of the invention, the compounds of the formula I areadministered in combination with insulin.

In an embodiment, the compounds of the formula I are administered incombination with a sulfonylurea, such as, for example, tolbutamide,glibenclamide, glipizide or glimepiride.

In an embodiment, the compounds of the formula I are administered incombination with a biguanide, such as, for example, metformin.

In another embodiment, the compounds of the formula I are administeredin combination with a meglitinide, such as, for example, repaglinide.

In an embodiment, the compounds of the formula I are administered incombination with a thiazolidinedione, such as, for example,troglitazone, ciglitazone, pioglitazone, rosiglitazone or the compoundswhich are disclosed by Dr. Reddy's Research Foundation in WO 97/41097,in particular5-[[4-[(3,4-dihydro-3-methyl-4-oxo-2-quinazolinylmethoxy]phenyl]methyl]-2,4-thiazolidinedione.

In an embodiment, the compounds of the formula I are administered incombination with an α-glucosidase inhibitor, such as, for example,miglitol or acarbose.

In an embodiment, the compounds of the formula I are administered incombination with an active ingredient which acts on the ATP-dependentpotassium channel of the beta cells, such as, for example, tolbutamide,glibenclamide, glipizide, glimepiride or repaglinide.

In an embodiment, the compounds of the formula I are administered incombination with more than one of the above-mentioned compounds, forexample in combination with a sulfonylurea and metformin, a sulfonylureaand acarbose, repaglinide and metformin, insulin and a sulfonylurea,insulin and metformin, insulin and troglitazone, insulin and lovastatin,etc.

In a further embodiment, the compounds of the formula I are administeredin combination with CART modulators (see “Cocaine-amphetamine-regulatedtranscript influences energy metabolism, anxiety and gastric emptying inmice” Asakawa, A, et al., M.: Hormone and Metabolic Research (2001),33(9), 554-558), NPY antagonists, for example naphthalene-1-sulfonicacid {4-[(4-aminoquinazolin-2-ylamino)methyl]cyclohexylmethyl}-amide;hydrochloride (CGP 71683A)), MC4 agonists (for example1-amino-1,2,3,4-tetra-hydronaphthalene-2-carboxylic acid[2-(3a-benzyl-2-methyl-3-oxo-2,3,3a,4,6,7-hexahydropyrazolo[4,3-c]pyridin-5-yl)-1-(4-chlorophenyl)-2-oxoethyl]amide;(WO 01/91752)), orexin antagonists (for example1-(2-methylbenzoxazol-6-yl)-3-[1,5]naphthyridin-4-ylurea; hydrochlorides(SB-334867-A)), H3 agonists(3-cyclohexyl-1-(4,4-dimethyl-1,4,6,7-tetra-hydro-imidazo[4,5-c]pyridin-5-yl)propan-1-oneoxalic acid salt (WO 00/63208)); TNF agonists, CRF antagonists (forexample[2-methyl-9-(2,4,6-trimethyl-phenyl)-9H-1,3,9-triazafluoren-4-yl]dipropylamine(WO 00/66585)), CRF BP antagonists (for example urocortin), urocortinagonists, β3-agonists (for example1-(4-chloro-3-methanesulfonylmethylphenyl)-2-[2-(2,3-dimethyl-1H-indol-6-yloxy)ethylamino]ethanol;hydrochlorides (WO 01/83451)), MSH (melanocyte-stimulating hormone)agonists, CCK-A agonists (for example{2-[4-(4-chloro-2,5-dimethoxyphenyl)-5-(2-cyclohexylethyl)thiazol-2-ylcarbamoyl]-5,7-dimethylindol-1-yl}aceticacid trifluoroacetic acid salt (WO 99/15525)); serotonin reuptakeinhibitors (for example dexfenfluramines), mixed serotonin compounds andnoradrenergic compounds (for example WO 10 00/71549), 5HT agonists, forexample 1-(3-ethylbenzo-furan-7-yl)piperazine oxalic acid salt (WO01/09111), bombesin agonists, galanin antagonists, growth hormone (forexample human growth hormone), growth hormone-releasing compounds(tert-butyl6-benzyloxy-1-(2-diisopropylaminoethylcarbamoyl)-3,4-dihydro-1H-isoquinoline-2-carboxylate(WO 01/85695)), TRH agonists (see, for example, EP 0 462 884) uncouplingprotein 2- or 3-modulators, leptin agonists (see, for example, Lee,Daniel W.; Leinung, Matthew C.; Rozhayskaya-Arena, Marina; Grasso,Patricia. Leptin agonists as a potential approach to the treatment ofobesity, Drugs of the Future (2001), 26(9), 873-881), DA agonists(bromocriptine, doprexin), lipase/amylase inhibitors (for example WO00/40569), PPAR modulators (for example WO 00/78312), RXR modulators orTR β-agonists.

In an embodiment of the invention, the further active ingredient isleptin; see, for example, “Perspectives in the therapeutic use ofleptin”, Salvador, Javier; Gomez Ambrosi, Javier; Fruhbeck, Gema, ExpertOpinion on Pharmacotherapy (2001), 2(10), 1615-1622.

In an embodiment, the additional active ingredient is dexamphetamine oramphetamine.

In an embodiment, the additional active ingredient is fenfluramine ordexfenfluramine.

In yet another embodiment, the additional active ingredient issibutramine.

In an embodiment, the additional active ingredient is orlistat.

In an embodiment, the additional active ingredient is mazindol orphentermine.

In an embodiment, the compounds of the formula I are administered incombination with bulk materials, preferably insoluble bulk materials(see, for example, Carob/Caromax® (Zunft H J; et al., Carob pulppreparation for treatment of hypercholesterolemia, ADVANCES IN THERAPY(2001 September-October), 18(5), 230-6.) Caromax is a carob-containingproduct from Nutrinova, Nutrition Specialties & Food Ingredients GmbH,Industriepark Höchst, 65926 Frankfurt/Main)). The combination withCaromax® can be effected in a single composition or by administration ofcompounds of the formula I and Caromax® separately. In this connection,Caromax® can also be administered in the form of foods, such as, forexample, in bakery products or muesli bars.

It goes without saying that each suitable combination of the compoundsaccording to the invention with one or more of the above-mentionedcompounds and optionally one or more further pharmacologically activesubstances is regarded as falling within the scope of protective of thepresent invention.

The invention also relates to a set (kit) consisting of separate packsof

-   (a) an effective amount of a compound of the formula I and/or    pharmaceutically usable derivatives, solvates, salts and    stereoisomers thereof, including mixtures thereof in all ratios, and-   (b) an effective amount of a further medicament active ingredient.

The set comprises suitable containers, such as boxes or cartons,individual bottles, bags or ampoules. The set may, for example, compriseseparate ampoules, each containing an effective amount of a compound ofthe formula I and/or pharmaceutically usable derivatives, solvates andstereoisomers thereof, including mixtures thereof in all ratios, and aneffective amount of a further medicament active ingredient in dissolvedor lyophilised form.

The compounds can be tested on their SGLT inhibition properties by meansof BHK cells expressing SGLT1 and SGLT2. The production of the cells andthe testing can be carried out as described below.

Construction and Expression of SGLT1 in BHK Cells

To construct the SGLT1 expression vector (KL225), the SLC5A1 gene(homologous to NM_(—)000343) was amplified from a cDNA library usingstandard PCR technology and cloned over NheI/XhoI sites into pcDNA3.1expression vector (Invitrogen) containing neomycin as a selectionmarker. In this vector, transcription uses the enhancer/promoter ofhuman cytomegalovirus.

The final vector KL225 together with an additional vector containing adihydrofolate reductase gene as a selection marker was introduced intocells. Transfection into BHK21 cells (ATCC CCL-10), cultivated in DMEMmedium (GIBCO/BRL), supplemented with 10% foetal calf serum (FCS) and 20mM glutamine, was carried out using calcium phosphate transfectionsaccording to Graham, F. L. and van der Ebb, A. J. (1973), Virology 52:456 with 5-20 μg of uncut plasmids for 10⁷ cells. Stable transfectantswere selected in medium containing 1 mg/ml of G418 (GIBCO/BRL) and20-5000 nM methotrexate as final concentration, where only cells whichexpressed the neomycin gene and overexpressed the dhfr gene were able togrow. After growth for 2-3 weeks, the cells were cloned (0.5 cells/well)and the clones were investigated for SGLT expression in the radioactiveuptake assay.

Construction and Expression of SGLT2 in BHK Cells

To construct the SGLT2 expression vector (KL224), the SLC5A2 gene(homologous to NM_(—)003041) was amplified from a cDNA library usingstandard PCR technology and cloned over NheI/XhoI sites into PCI-neoexpression vector (Promega) containing neomycin as a selection marker.In this vector, transcription used the enhancer/promoter of humancytomegalovirus and the SV40 polyadenylation signal.

The final vector KL224 together with an additional vector containing adihydrofolate reductase gene as a selection marker was introduced intocells. Transfection into BHK21 cells (ATCC CCL-10), cultivated in DMEMmedium (GIBCO/BRL), supplemented with 10% foetal calf serum (FCS) and 20mM glutamine, was carried out using calcium phosphate transfectionsaccording to Graham, F. L. and van der Ebb, A. J. (1973), Virology 52:456 with 5-20 μg of uncut plasmids for 10⁷ cells. Stable transfectantswere selected in medium containing 1 mg/ml of G418 (GIBCO/BRL) and20-5000 nM methotrexate as final concentration, where only cells whichexpressed the neomycin gene and overexpressed the dhfr gene were able togrow. After growth for 2-3 weeks, the cells were cloned (0.5 cells/well)and the clones were investigated for SGLT expression in the radioactiveuptake assay.

Method of SGLT1/2 Activity Measurement

Principally, uptake of ¹⁴C-α-methyl-D-glucopyranoside (AMG) in, forexample, Xenopus oocytes injected with the corresponding cRNA has beendescribed (for example Wen-Sen Lee et al. (1994), J. Biol. Chem. 269,12032-12039; Guofeng You et al. (1995), J. Biol. Chem. 270,29365-29371).

A 96-well cell-based assay was developed and adapted to HTSrequirements:

BHK cells (transfected with SGLT1 or SGLT2) were seeded into 96-wellmicrotitre plates (Cultureplates, Perkin Elmer). After at least 24 h,medium was removed and the cell layer was washed with assay buffer (140mM NaCl, 2 mM KCl, 1 mM CaCl₂, 1 mM MgCl₂, 10 mM HEPES, 5 mM Tris,adjusted with 1 M KOH to pH 7.4). After addition of 40 μl of assaybuffer, 50 μl of AMG (50 μM for SGLT1 and 2 mM for SGLT2) in thepresence or absence of compounds, the cells were incubated in a totalvolume of 100 μl at 37° C. for 90 min. Supernatant was removed bysuction and discarded. The cells were washed and lysed by addition of 50μl water. After 10 minutes at room temperature 200 μl Microscint 40(Perkin Elmer) were added. The radioactivity was counted in a Topcountmicroplate scintillation counter (Perkin Elmer). The non-specific uptakewas determined in sodium-free assay buffer (266 mM sucrose, 2 mM KCl, 1mM CaCl₂, 1 mM MgCl₂, 10 mM HEPES, 5 mM Tris, adjusted with 1 M KOH topH 7.4).

Above and below, all temperatures are indicated in ° C. In the followingexamples, “conventional work-up” means: water is added if necessary, thepH is adjusted, if necessary, to values between 2 and 10, depending onthe constitution of the end product, the mixture is extracted with ethylacetate or dichloromethane, the phases are separated, the organic phaseis dried over sodium sulfate and evaporated, and the product is purifiedby chromatography on silica gel and/or by crystallisation. Rf values onsilica gel; eluent: ethyl acetate/methanol 9:1.

Mass spectrometry (MS): EI (electron impact ionisation) M⁺

FAB (fast atom bombardment) (M+H)⁺

ESI (electrospray ionisation) (M+H)⁺ (unless indicated otherwise)

EXAMPLE 1

The preparation of2-[2-(aminocarbonylmethoxy)-6-methoxyphenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridine(“A1”) is carried out analogously to the following scheme:

1.1 1.0 g (6.57 mmol) of 2-hydroxy-6-methoxybenzaldehyde 1 is dissolvedin 30 ml of DMF, 0.29 g of NaH (60% suspension in paraffin oil) iscarefully added with cooling, and the mixture is stirred at RT for 45min. 1.34 g of 2-iodoacetamide 2 are then added, and the reactionmixture is stirred overnight. The mixture is subsequently subjected toconventional work-up, giving 0.81 g (59%) of2-(2-formyl-3-methoxyphenoxy)acetamide 3 as solid. MS-EI (M⁺)=209.

1.2 Analogously to H. Bienaymé et al. Angew. Chem. 1998, 100, 2349:0.207 g of 2-amino-5-fluoropyridine 4 and 0.33 g of the aldehyde 3 aredissolved successively in 30 ml of ethanol at RT under an inert gas.0.24 g of 2,6-dimethylphenylisocyanide 5 is then added, 0.075 ml of 70%perchloric acid is added dropwise, and the mixture is stirred at RT fora further 20 h. The mixture is subsequently subjected to conventionalwork-up, giving 0.42 g (55%) of “A1”; m.p. 103-104°; MS-EI (M⁺)=434.

¹H-NMR (DMSO-d₆) δ 8.09 (1H, dd, J=2.4 and 4.3 Hz), 8.03 (N—H, s), 7.51(1H, dd, J=5.1 and 9.7 Hz), 7.38 (N—H, s), 7.26 (1H, ddd, J=2.4, 8.5 and9.7 Hz), 7.15 (1H, t, J=8.4 Hz), 6.73 (2H, d, J=7.4 Hz), 6.65 (N—H, s),6.58 (1H, t, J=7.4 Hz), 6.55 (1H, d, J=8.4 Hz), 6.48 (1H, d, J=8.4 Hz),4.36 (2H, s), 3.57 (3H, s), 1.85 (6H, s).

EXAMPLE 2

The preparation of2-[2-(aminocarbonylmethoxy)-6-methylphenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridine(“A2”) is carried out analogously to the following scheme:

2.1 19.95 g of 2,3-dimethylphenol 6 are dissolved in 250 ml of DMF, 6.4g of NaH (60% suspension in paraffin oil) are carefully added withcooling, and the mixture is stirred at RT for 45 min. 31.4 g of2-iodoacetamide 2 are then added, and the reaction mixture is stirredovernight. The mixture is subsequently subjected to conventionalwork-up, giving 23.8 g (83%) of 2-(2,3-dimethylphenoxy)acetamide 7;MS-EI (M⁺)=179.

2.2 Analogously to FM Hauser and SR Ellenberger Synthesis 1987, 723:

12.0 g of 7, 50.82 g of potassium peroxodisulfate and 17.05 g ofcopper(II) sulfate pentahydrate are dissolved in a solvent mixturecomprising 250 ml of MeCN and 250 ml of water, and the mixture issubsequently stirred under reflux for 2 h. The mixture is then subjectedto conventional work-up, giving 1.38 g (11%) of2-(2-formyl-3-methylphenoxy)acetamide 8; MS-EI (M⁺)=193.

2.3 0.095 g of 2-amino-5-fluoropyridine 4 and 0.14 g of the aldehyde 8are dissolved successively in 30 ml of ethanol at RT under an inert gas.0.11 g of 2,6-dimethylphenylisocyanide 5 is then added, 34.43 μl of 70%perchloric acid are added dropwise, and the mixture is stirred at RT fora further 20 h. The mixture is subsequently subjected to conventionalwork-up, giving 0.084 g (25%) of “A2”; m.p. 198-199°; MS-EI (M⁺)=418.

¹H-NMR (DMSO-d₆) δ 7.74 (1H, dd, J=2.4 and 4.1 Hz), 7.58 (1H, dd, J=5.1and 9.7 Hz), 7.47 (N—H, s), 7.42 (N—H, s), 7.23 (1H, ddd, J=2.4, 8.5 and9.7 Hz), 7.16 (1H, t, J=8.0 Hz), 7.00 (N—H, s), 6.83 (1H, d, J=7.5 Hz),6.82 (2H, d, J=7.4 Hz), 6.69 (1H, t, J=7.4 Hz), 6.68 (1H, d, J=7.5 Hz),4.38 (2H, s), 2.12 (3H, s), 1.84 (6H, s).

EXAMPLE 3

The preparation of2-[2-(aminocarbonylmethoxy)-6-chlorophenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridine(“A3”) is carried out analogously to the following scheme:

3.1 1.0 g of 6-chlorosalicylaldehyde 9 is dissolved in 30 ml of DMF,0.26 g of NaH (60% suspension in paraffin oil) is carefully added withcooling, and the mixture is stirred at RT for 45 min. 1.30 g of2-iodoacetamide 2 are then added, and the reaction mixture is stirredovernight. The mixture is subsequently subjected to conventionalwork-up, giving 1.28 g (90%) of 2-(3-chloro-2-formylphenoxy)acetamide10; MS-EI (M⁺)=213.

3.2 0.177 g of 2-amino-5-fluoropyridine 4 and 0.288 g of the aldehyde 10are dissolved successively in 30 ml of ethanol at RT under an inert gas.0.205 g of 2,6-dimethylphenylisocyanide 5 is then added, 64.1 μl of 70%perchloric acid are added dropwise, and the mixture is stirred at RT fora further 20 h. The mixture is subsequently subjected to conventionalwork-up, giving 0.286 g (43%) of “A3”; m.p. 186-187°; MS-EI (M⁺)=438.

¹H-NMR (DMSO-d₆) δ 8.05 (1H, dd, J=2.4 and 4.1 Hz), 7.58 (1H, dd, J=5.1and 9.7 Hz), 7.48 (N—H, s), 7.42 (N—H, s), 7.29 (1H, ddd, J=2.4, 8.5 and9.7 Hz), 7.21 (1H, t, J=8.2 Hz), 7.00 (1H, d, J=8.2 Hz), 6.91 (N—H, s),6.81 (1H, d, J=8.2 Hz), 6.75 (2H, d, J=7.4 Hz), 6.62 (1H, t, J=7.4 Hz),4.41 (1H, d, J=15.1 Hz), 4.31 (1H, d, J=15.1 Hz), 1.87 (6H, s).

EXAMPLE 4

Alternative preparation of2-[2-(aminocarbonylmethoxy)-6-methoxyphenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridine(“A1”):

4.1 10.0 g of sodium acetate are dissolved in 120 ml of formic acid.50.0 g of 2,6-dimethylaniline 11 are then introduced, and the mixture isstirred under reflux for 24 h. The mixture is subsequently subjected toconventional work-up, giving 48.9 g (79%) ofN-(2,6-dimethylphenyl)formamide 12; MS-EI (M⁺)=149.

4.2 0.149 g of 12, 0.112 g of 2-amino-5-fluoropyridine 4, 0.209 g of2-(2-formyl-3-methoxyphenoxy)acetamide 3, 0.286 ml of triethylamine and,dropwise, 2.5 ml of T3P® [=propylphosphonic anhydride (50% solution inethyl acetate)] are introduced successively into a flask withice-cooling and under an inert gas. The reaction mixture is stirred at100° C. for 7 h. The mixture is subsequently subjected to conventionalwork-up, giving 0.2 g (40%) of “A1”.

The following compounds are obtained analogously to Example 1, 2 or 3

No. Name and/or structure MS-EI (M⁺) “A4”2-[2-(Aminocarbonylmethoxy)phenyl]-3-(2,6-di- 386methylphenylamino)imidazo[1,2-a]pyridine “A5”2-[2-(Aminocarbonylmethoxy)phenyl]-3-(2,6-di- 426chlorophenylamino)imidazo[1,2-a]pyridine “A6”2-[2-(Aminocarbonylmethoxy)phenyl]-3- 406(2-chloro-6-methylphenylamino)imidazo[1,2-a]-pyridine “A7”2-[2-(Aminocarbonylmethoxy)phenyl]-3- 414(2-isopropyl-6-methylphenylamino)imidazo-[1,2-a]pyridine “A8”2-[2-(Aminocarbonylmethoxy)phenyl]-3-(2,6-di- 400methylphenylamino)-8-methylimidazo[1,2-a]-pyridine “A9”2-[2-(Aminocarbonylmethoxy)phenyl]-3-(2,6-di- 400methylphenylamino)-5-methylimidazo[1,2-a]-pyridine “A10”2-[2-(Aminocarbonylmethoxy)phenyl]-3- 420(2-chloro-6-methylphenylamino)-5-methyl- imidazo[1,2-a]pyridine “A11”2-[2-(Aminocarbonylmethoxy)phenyl]-3-(2,6-di- 440chlorophenylamino)-5-methylimidazo[1,2-a]-pyridine “A12”2-[2-(Aminocarbonylmethoxy)phenyl]-3-(2,6- 420dimethylphenylamino)-5-chloroimidazo[1,2-a]-pyridine “A13”2-[2-(Aminocarbonylmethoxy)phenyl]-3-(2,6- 414dimethylphenylamino)-5-ethylimidazo[1,2-a]-pyridine “A14”2-[2-(Aminocarbonylmethoxy)-4-methoxy- 416phenyl]-3-(2,6-dimethylphenylamino)imidazo-[1,2-a]pyridine “A15”2-[2-(Aminocarbonylmethoxy)-4-methoxy- 436phenyl]-3-(2-chloro-6-methylphenylamino)- imidazo[1,2-a]pyridine “A16”2-[2-(Aminocarbonylmethoxy)-4-methoxy- 456phenyl]-3-(2,6-dichlorophenylamino)imidazo-[1,2-a]pyridine “A17”2-[2-(Aminocarbonylmethoxy)-4-methylphenyl]- 4003-(2,6-dimethylphenylamino)-imidazo[1,2-a]-pyridine “A18”2-[2-(Aminocarbonylmethoxy)-5-methoxy- 416phenyl]-3-(2,6-dimethylphenylamino)imidazo-[1,2-a]pyridine “A19”2-[2-(Aminocarbonylmethoxy)-5-methylphenyl]- 4003-(2,6-dimethylphenylamino)imidazo[1,2-a]-pyridine “A20”2-[2-(Aminocarbonylmethoxy)-6-methylphenyl]- 4003-(2,6-dimethylphenylamino)imidazo[1,2-a]-pyridine “A21”2-[2-(Aminocarbonylmethoxy)-6-chlorophenyl]-3- 420(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A22”2-[2-(Aminocarbonylmethoxy)-6-methoxy- 416phenyl]-3-(2,6-dimethylphenylamino)imidazo-[1,2-a]pyridine “A23”2-[2-(Aminocarbonylmethoxy)-6-methoxy- 436phenyl]-3-(2-chloro-6-methylphenylamino)- imidazo[1,2-a]pyridine “A24”2-[2-(Aminocarbonylmethoxy)-6-methoxy- 456phenyl]-3-(2,6-dichlorophenylamino)imidazo-[1,2-a]pyridine “A25”2-[2-(Aminocarbonylmethoxy)phenyl]-3-(2,6- 404dimethylphenylamino)-6-fluoroimidazo[1,2-a]-pyridine “A26”2-[2-(Aminocarbonylmethoxy)phenyl]-3-(2,6- 404dimethylphenylamino)-8-fluoroimidazo[1,2-a]-pyridine “A27”2-[2-(Aminocarbonylmethoxy)-3-fluorophenyl]-3- 404(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A28”2-[2-(Aminocarbonylmethoxy)-4-fluorophenyl]-3- 404(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A29”2-[2-(Aminocarbonylmethoxy)phenyl]-3-(2,6- 404dimethylphenylamino)-5-fluoroimidazo[1,2-a]-pyridine “A30”2-[2-(Aminocarbonylmethoxy)phenyl]-3-(2,6- 422dimethylphenylamino)-6,8-difluoroimidazo-[1,2-a]pyridine “A31”2-[2-(Aminocarbonylmethoxy)-5-fluorophenyl]-3- 404(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A32”2-[2-(Aminocarbonylmethoxy)-6-fluorophenyl]-3- 404(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A33”2-[2-(Aminocarbonylmethoxy)-6-fluorophenyl]-3- 422(2,6-dimethylphenylamino)-6-fluoroimidazo-[1,2-a]pyridine “A34”2-[2-(Aminocarbonylmethoxy)-4-fluorophenyl]-3- 422(2,6-dimethylphenylamino)-6-fluoroimidazo-[1,2-a]pyridine “A35”2-[2-(Aminocarbonylmethoxy)-4-fluorophenyl]-3- 422(2,6-dimethylphenylamino)-5-fluoroimidazo-[1,2-a]pyridine “A36”2-[2-(Aminocarbonylmethoxy)-6-methoxy- 434phenyl]-3-(2,6-dimethylphenylamino)-5-fluoro- imidazo[1,2-a]pyridine“A37” 2-[2-(Aminocarbonylmethoxy)-6-methoxy- 452phenyl]-3-(2,6-dimethylphenylamino)-6,8- difluoroimidazo[1,2-a]pyridine“A38” 2-[2-(Aminocarbonylmethoxy)phenyl]-3-(2-ethyl- 4006-methylphenylamino)imidazo[1,2-a]pyridine “A39”2-[2-(Aminocarbonylmethoxy)-6-methoxy- 430phenyl]-3-(2-ethyl-6-methylphenylamino)- imidazo[1,2-a]pyridine “A40”2-[2-(Aminocarbonylmethoxy)phenyl]-3-(2,6- 414diethylphenylamino)imidazo[1,2-a]pyridine “A41”2-[2-(Aminocarbonylmethoxy)-6-methoxy- 444phenyl]-3-(2,6-diethylphenylamino)imidazo-[1,2-a]pyridine “A42”2-[2-(Aminocarbonylmethoxy)phenyl]-3-(2,4,6- 400trimethylphenylamino)imidazo[1,2-a]pyridine “A43”2-[2-(Aminocarbonylmethoxy)phenyl]-3-(2,4,6- 418trimethylphenylamino)-6-fluoroimidazo[1,2-a]-pyridine “A44”2-[2-(Aminocarbonylmethoxy)phenyl]-3-(2,4,6- 418trimethylphenylamino)-5-fluoroimidazo[1,2-a]-pyridine “A45”2-[2-(Aminocarbonylmethoxy)-6-methoxy- 448phenyl]-3-(2,4,6-trimethylphenylamino)-6-fluoro- imidazo[1,2-a]pyridine“A46” 2-[2-(Aminocarbonylmethoxy)-6-fluorophenyl]-3- 440(2,6-dimethyl-4-fluorophenylamino)-6-fluoro- imidazo[1,2-a]pyridine“A47” 2-[2-(Aminocarbonylmethoxy)phenyl]-3-(2,6- 404dimethyl-4-fluorophenylamino)imidazo[1,2-a]-pyridine “A48”2-[2-(Aminocarbonylmethoxy)-6-methoxy- 434phenyl]-3-(2,6-dimethylphenylamino)-8-fluoro- imidazo[1,2-a]pyridine“A49” 2-[2-(Aminocarbonylmethoxy)phenyl]-3-(2,6- 422dimethyl-4-fluorophenylamino)-6-fluoroimidazo-[1,2-a]pyridine “A50”2-[2-(Aminocarbonylmethoxy)phenyl]-3-(2-ethyl- 4186-methylphenylamino)-6-fluoroimidazo[1,2-a]-pyridine “A51”2-[2-(Aminocarbonylmethoxy)phenyl]-3-(2-ethyl- 4366-methylphenylamino)-6,8-difluoroimidazo-[1,2-a]pyridine “A52”2-[2-(Aminocarbonylmethoxy)-6-methylphenyl]- 4183-(2,6-dimethylphenylamino)-8-fluoroimidazo-[1,2-a]pyridine “A53”2-[2-(Aminocarbonylmethoxy)-6-methylphenyl]- 4363-(2,6-dimethylphenylamino)-6,8-difluoro- imidazo[1,2-a]pyridine “A54”2-[2-(Aminocarbonylmethoxy)-4-chlorophenyl]-3- 420(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A55”2-[2-(Aminocarbonylmethoxy)-6-methylphenyl]- 4323-(2-ethyl-6-methylphenylamino)-6-fluoro- imidazo[1,2-a]pyridine “A56”2-[2-(Aminocarbonylmethoxy)-4-chlorophenyl]-3- 438(2,6-dimethylphenylamino)-6-fluoroimidazo-[1,2-a]pyridine “A57”2-[2-(Aminocarbonylmethoxy)phenyl]-3-(2,6-dimethylphenylamino)-6,8-difluoroimidazo-[1,2-a]pyridine “A58”2-[2-(Aminocarbonylmethoxy)-4-fluorophenyl]-3-(2,6-dimethyl-4-fluorophenylamino)-6-fluoro- imidazo[1,2-a]pyridine“A59” 2-[2-(Aminocarbonylmethoxy)-6-methylphenyl]-3-(2,6-dimethyl-4-fluorophenylamino)-6-fluoro- imidazo[1,2-a]pyridine“A60” 2-[2-(Aminocarbonylmethoxy)-4-cyanophenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo-[1,2-a]pyridine “A61”2-[2-(Aminocarbonylmethylamino)phenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine  

“A62” 2-[2-(Ureidomethyl)phenyl]-3-(2,6-dimethyl-phenylamino)imidazo[1,2-a]pyridine  

“A63” 2-[2-(Aminocarbonylmethylamino)phenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]-pyridine “A64”2-[2-(Ureidomethyl)phenyl]-3-(2,6-dimethyl-phenylamino)-6-fluoroimidazo[1,2-a]pyridine “A65”2-[2-(Aminocarbonylmethylamino)phenyl]-3-(2,6-dimethylphenylamino)-6,8-difluoroimidazo-[1,2-a]pyridine “A66”2-[2-(Ureidomethyl)phenyl]-3-(2,6-dimethyl-phenylamino)-6,8-difluoroimidazo[1,2-a]pyridine “A67”2-[2-(Aminocarbonylmethoxy)-5-fluorophenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A68”2-[2-(Aminocarbonylmethoxy)-5-chlorophenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A69”2-[2-(Aminocarbonylmethoxy)-5-nitrophenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A70”2-[2-(Aminocarbonylmethoxy)-5-aminophenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A71”2-[2-(Aminocarbonylmethoxy)-5-fluorophenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo-[1,2-a]pyridine “A72”2-[2-(Aminocarbonylmethoxy)-5-chlorophenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo-[1,2-a]pyridine “A73”2-[2-(Aminocarbonylmethoxy)-5-nitrophenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo-[1,2-a]pyridine “A74”2-[2-(Aminocarbonylmethoxy)-5-aminophenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo-[1,2-a]pyridine “A75”2-[2-(Aminocarbonylmethoxy)-4-hydroxyphenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]-pyridine “A76”2-[2-(Aminocarbonylmethoxy)-4,6-dimethyl-phenyl]-3-(2,6-dimethylphenylamino)imidazo-[1,2-a]pyridine “A77”2-[2-(Aminocarbonylmethoxy)-4-bromophenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A78”2-[2-(Aminocarbonylmethoxy)-4-cyanophenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A79”2-[2-(Aminocarbonylmethoxy)-4-hydroxyphenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo-[1,2-a]pyridine “A80”2-[2-(Aminocarbonylmethoxy)-4-bromophenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo-[1,2-a]pyridine “A81”2-[2-(Aminocarbonylmethoxy)-4-chlorophenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo-[1,2-a]pyridine “A82”2-[2-(Aminocarbonylmethoxy)-4-methylphenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo-[1,2-a]pyridine “A83”2-[2-(Aminocarbonyloxy)phenyl]-3-(2,6-dimethyl-phenylamino)imidazo[1,2-a]pyridine  

“A84” 2-[2-(Aminocarbonyloxymethyl)phenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A85”2-[2-(Methylaminocarbonylmethoxy)phenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A86”2-[2-(Dimethylaminocarbonylmethoxy)phenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A87”2-{2-[2-(Aminocarbonyl)ethoxy]phenyl}-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A88”2-[2-(Aminocarbonyloxy)phenyl]-3-(2,6-dimethyl-phenylamino)-6-fluoroimidazo[1,2-a]pyridine “A89”2-[2-(Aminocarbonyloxymethyl)phenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]-pyridine “A90”2-[2-(Methylaminocarbonylmethoxy)phenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo-[1,2-a]pyridine “A91”2-[2-(Dimethylaminocarbonylmethoxy)phenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo-[1,2-a]pyridine “A92”2-{2-[2-(Aminocarbonyl)ethoxy]phenyl}-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]-pyridine “A93”2-[2-(Aminocarbonylmethoxy)-6-cyano-4-hydroxyphenyl]-3-(2,6-dimethylphenylamino)- imidazo[1,2-a]pyridine “A94”2-[2-(Aminocarbonylmethoxy)-6-chloro-4-hydroxyphenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridine “A95”2-[2-(Aminocarbonylmethoxy)-6-bromo-4-hydroxyphenyl]-3-(2,6-dimethylphenylamino)- imidazo[1,2-a]pyridine “A96”2-[2-(Aminocarbonylmethoxy)-6-methyl-4-hydroxyphenyl]-3-(2,6-dimethylphenylamino)- imidazo[1,2-a]pyridine “A97”2-[2-(Aminocarbonylmethoxy)-6-ethyl-4-hydroxy-phenyl]-3-(2,6-dimethylphenylamino)imidazo-[1,2-a]pyridine “A98”2-[2-(Aminocarbonylmethoxy)-6-cyano-4-hydroxyphenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridine “A99”2-[2-(Aminocarbonylmethoxy)-6-chloro-4-hydroxyphenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridine “A100”2-[2-(Aminocarbonylmethoxy)-6-bromo-4-hydroxyphenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridine “A101”2-[2-(Aminocarbonylmethoxy)-6-methyl-4-hydroxyphenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridine “A102”2-[2-(Aminocarbonylmethoxy)-6-ethyl-4-hydroxy-phenyl]-3-(2,6-dimethylphenylamino)-6-fluoro- imidazo[1,2-a]pyridine“A103” 2-[2-(Aminocarbonylmethoxy)-6-methyl-4-(2-methylaminoacetoxy)phenyl]-3-(2,6-dimethyl-phenylamino)imidazo[1,2-a]pyridine  

“A104” 2-[2-(Aminocarbonylmethoxy)-6-methyl-4-(2-methylaminoacetoxy)phenyl]-3-(2,6-dimethyl-phenylamino)-6-fluoroimidazo[1,2-a]pyridine “A105”2-[2-(Aminocarbonylmethoxy)-6-methyl-4-(2-methylaminoacetylamino)phenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine  

“A106” 2-[2-(Aminocarbonylmethoxy)-6-methyl-4-(2-methylaminoacetylamino)phenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]-pyridine “A107”2-[2-(Aminocarbonylmethoxy)-4-(2-methyl-aminoacetoxy)phenyl]-3-(2,6-dimethylphenyl- amino)imidazo[1,2-a]pyridine“A108” 2-[2-(Aminocarbonylmethoxy)-4-(2-methyl-aminoacetoxy)phenyl]-3-(2,6-dimethylphenyl-amino)-6-fluoroimidazo[1,2-a]pyridine “A109”2-[2-(Aminocarbonylmethoxy)-4-(2-methyl-aminoacetylamino)phenyl]-3-(2,6-dimethyl-phenylamino)imidazo[1,2-a]pyridine “A110”2-[2-(Aminocarbonylmethoxy)-4-(2-methyl-aminoacetylamino)phenyl]-3-(2,6-dimethyl-phenylamino)-6-fluoroimidazo[1,2-a]pyridine “A111”2-[2-(Aminocarbonylmethoxy)-4-(2-amino-ethoxy)-6-chlorophenyl]-3-(2,6-dimethylphenyl-amino)imidazo[1,2-a]pyridine  

“A112” 2-[2-(Aminocarbonylmethoxy)-4-(2-methylamino-ethoxy)-6-chlorophenyl]-3-(2,6-dimethylphenyl-amino)imidazo[1,2-a]pyridine “A113”2-[2-(Aminocarbonylmethoxy)-4-(2-dimethyl-aminoethoxy)-6-chlorophenyl]-3-(2,6-dimethyl-phenylamino)imidazo[1,2-a]pyridine “A114”2-[2-(Aminocarbonylmethoxy)-4-(2-amino-ethoxy)-6-chlorophenyl]-3-(2,6-dimethylphenyl-amino)-6-fluoroimidazo[1,2-a]pyridine “A115”2-[2-(Aminocarbonylmethoxy)-4-(2-methylamino-ethoxy)-6-chlorophenyl]-3-(2,6-dimethylphenyl-amino)-6-fluoroimidazo[1,2-a]pyridine “A116”2-[2-(Aminocarbonylmethoxy)-4-(2-dimethyl-aminoethoxy)-6-chlorophenyl]-3-(2,6-dimethyl-phenylamino)-6-fluoroimidazo[1,2-a]pyridine “A117”2-[2-(Aminocarbonylmethoxy)-4-(2-amino-ethoxy)-6-methylphenyl]-3-(2,6-dimethylphenyl-amino)imidazo[1,2-a]pyridine “A118”2-[2-(Aminocarbonylmethoxy)-4-(2-methylamino-ethoxy)-6-methylphenyl]-3-(2,6-dimethylphenyl-amino)imidazo[1,2-a]pyridine “A119”2-[2-(Aminocarbonylmethoxy)-4-(2-dimethyl-aminoethoxy)-6-methylphenyl]-3-(2,6-dimethyl-phenylamino)imidazo[1,2-a]pyridine “A120”2-[2-(Aminocarbonylmethoxy)-4-(2-amino-ethoxy)-6-methylphenyl]-3-(2,6-dimethylphenyl-amino)-6-fluoroimidazo[1,2-a]pyridine “A121”2-[2-(Aminocarbonylmethoxy)-4-(2-methylamino-ethoxy)-6-methylphenyl]-3-(2,6-dimethylphenyl-amino)-6-fluoroimidazo[1,2-a]pyridine “A122”2-[2-(Aminocarbonylmethoxy)-4-(2-dimethyl-aminoethoxy)-6-methylphenyl]-3-(2,6-dimethyl-phenylamino)-6-fluoroimidazo[1,2-a]pyridine “A123”2-[2-(Aminocarbonylmethoxy)-6-bromophenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A124”2-[2-(Aminocarbonylmethoxy)-6-nitrophenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A125”2-[2-(Aminocarbonylmethoxy)-6-cyanophenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A126”2-[2-(Aminocarbonylmethoxy)-6-carboxyphenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]-pyridine “A127”2-[2-(Aminocarbonylmethoxy)-6-hydroxymethyl-phenyl]-3-(2,6-dimethylphenylamino)imidazo-[1,2-a]pyridine “A128”2-[2-(Aminocarbonylmethoxy)-6-bromophenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo-[1,2-a]pyridine “A129”2-[2-(Aminocarbonylmethoxy)-6-nitrophenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo-[1,2-a]pyridine “A130”2-[2-(Aminocarbonylmethoxy)-6-cyanophenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo-[1,2-a]pyridine “A131”2-[2-(Aminocarbonylmethoxy)-6-carboxyphenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo-[1,2-a]pyridine “A132”2-[2-(Aminocarbonylmethoxy)-6-hydroxymethyl-phenyl]-3-(2,6-dimethylphenylamino)-6-fluoro- imidazo[1,2-a]pyridine“A133” 2-[2-(Aminocarbonylmethoxy)-6-(2-methylamino-ethoxymethyl)phenyl]-3-(2,6-dimethylphenyl- amino)imidazo[1,2-a]pyridine 

“A134” 2-[2-(Aminocarbonylmethoxy)-6-(2-methylamino-ethoxymethyl)phenyl]-3-(2,6-dimethylphenyl-amino)-6-fluoroimidazo[1,2-a]pyridine “A135”2-[2-(Aminocarbonylmethoxy)-6-(2-methylamino-ethoxymethyl)phenyl]-3-(2,6-dimethylphenyl-amino)-6,8-difluoroimidazo[1,2-a]pyridine “A136”2-[2-(Aminocarbonylmethoxy)-6-(2-methylamino-ethoxy)phenyl]-3-(2,6-dimethylphenylamino)- imidazo[1,2-a]pyridine“A137” 2-[2-(Aminocarbonylmethoxy)-6-aminophenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A138”2-[2-(Aminocarbonylmethoxy)-6-(2-methoxy-ethylamino)phenyl]-3-(2,6-dimethylphenyl- amino)imidazo[1,2-a]pyridine  

“A139” 2-[2-(Aminocarbonylmethoxy)-6-(2-hydroxyethyl-amino)phenyl]-3-(2,6-dimethylphenylamino)- imidazo[1,2-a]pyridine “A140”2-[2-(Aminocarbonylmethoxy)-6-(2-aminoethyl-amino)phenyl]-3-(2,6-dimethylphenylamino)- imidazo[1,2-a]pyridine “A141”2-[2-(Aminocarbonylmethoxy)-6-(2-methylamino-ethylamino)phenyl]-3-(2,6-dimethylphenyl- amino)imidazo[1,2-a]pyridine“A142” 2-[2-(Aminocarbonylmethoxy)-6-aminophenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo-[1,2-a]pyridine “A143”2-[2-(Aminocarbonylmethoxy)-6-(2-methoxy-ethylamino)phenyl]-3-(2,6-dimethylphenyl-amino)-6-fluoroimidazo[1,2-a]pyridine “A144”2-[2-(Aminocarbonylmethoxy)-6-(2-hydroxyethyl-amino)phenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridine “A145”2-[2-(Aminocarbonylmethoxy)-6-(2-aminoethyl-amino)phenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridine “A146”2-[2-(Aminocarbonylmethoxy)-6-(2-methylamino-ethylamino)phenyl]-3-(2,6-dimethylphenyl-amino)-6-fluoroimidazo[1,2-a]pyridine “A147”2-[2-(Aminocarbonylmethoxy)-6-aminophenyl]-3-(2,6-dimethylphenylamino)-6,8-difluoroimidazo-[1,2-a]pyridine “A148”2-[2-(Aminocarbonylmethoxy)-6-(2-methoxy-ethylamino)phenyl]-3-(2,6-dimethylphenyl-amino)-6,8-difluoroimidazo[1,2-a]pyridine “A149”2-[2-(Aminocarbonylmethoxy)-6-(2-hydroxyethyl-amino)phenyl]-3-(2,6-dimethylphenylamino)-6,8-difluoroimidazo[1,2-a]pyridine “A150”2-[2-(Aminocarbonylmethoxy)-6-(2-aminoethyl-amino)phenyl]-3-(2,6-dimethylphenylamino)-6,8-difluoroimidazo[1,2-a]pyridine “A151”2-[2-(Aminocarbonylmethoxy)-6-(2-methylamino-ethylamino)phenyl]-3-(2,6-dimethylphenyl-amino)-6,8-difluoroimidazo[1,2-a]pyridine “A152”2-[2-(Aminocarbonylmethoxy)-4-(2-amino-ethoxy)-6-bromophenyl]-3-(2,6-dimethylphenyl-amino)imidazo[1,2-a]pyridine “A153”2-[2-(Aminocarbonylmethoxy)-4-(2-amino-ethoxy)-6-cyanophenyl]-3-(2,6-dimethylphenyl-amino)imidazo[1,2-a]pyridine “A154”2-[2-(Aminocarbonylmethoxy)-4-(2-amino-ethoxy)-6-bromophenyl]-3-(2,6-dimethylphenyl-amino)-6-fluoroimidazo[1,2-a]pyridine “A155”2-[2-(Aminocarbonylmethoxy)-4-(2-amino-ethoxy)-6-cyanophenyl]-3-(2,6-dimethylphenyl-amino)-6-fluoroimidazo[1,2-a]pyridine “A156”2-[2-(Aminocarbonylmethoxy)-6-hydroxyphenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]-pyridine “A157”2-[2-(Aminocarbonylmethoxy)-6-hydroxyphenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo-[1,2-a]pyridine “A158”2-[2-(Aminocarbonylmethoxy)-6-(2-hydroxy-ethoxy)phenyl]-3-(2,6-dimethylphenylamino)- imidazo[1,2-a]pyridine“A159” 2-[2-(Aminocarbonylmethoxy)-6-(2-hydroxy-ethoxy)phenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridine “A160”2-[2-(Aminocarbonylmethoxy)-6-hydroxyphenyl]-3-(2,6-dimethylphenylamino)-6,8-difluoro- imidazo[1,2-a]pyridine “A161”2-[2-(Aminocarbonylmethoxy)-6-propylphenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A162”2-[2-(Aminocarbonylmethoxy)-6-propylphenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo-[1,2-a]pyridine “A163”2-[2-(Aminocarbonylmethoxy)-4-hydroxy-6-propylphenyl]-3-(2,6-dimethylphenylamino)- imidazo[1,2-a]pyridine “A164”2-[2-(Aminocarbonylmethoxy)-4-hydroxy-6-propylphenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridine “A165”2-[2-(Aminocarbonylmethoxy)-4-methyl-sulfonyloxy-6-methylphenyl]-3-(2,6-dimethyl-phenylamino)imidazo[1,2-a]pyridine  

“A166” 2-[2-(Aminocarbonylmethoxy)-4-(tetra-hydropyran-2-yloxy)-6-ethylphenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine  

“A167” 2-[2-(Aminocarbonylmethoxy)-4-(amino-carbonylmethoxy)-6-ethylphenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine  

“A168” 2-[2-(Aminocarbonylmethoxy)-4,6-dimethyl-phenyl]-3-(2,6-dimethylphenylamino)imidazo-[1,2-a]pyridine “A169”2-[2-(Aminocarbonylmethoxy)-4,6-dimethyl-phenyl]-3-(2,6-dimethylphenylamino)-6-fluoro- imidazo[1,2-a]pyridine“A170” 2-[2-(Aminocarbonylmethoxy)-4-(amino-carbonylmethoxy)-6-methylphenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A171”2-[2-(Aminocarbonylmethoxy)-4-hydroxy-6-methylphenyl]-3-(2,6-dimethylphenylamino)- imidazo[1,2-a]pyridine “A172”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methylphenyl]-3-(2,6-dimethylphenylamino)- imidazo[1,2-a]pyridine “A173”2-[2-(Aminocarbonylmethoxy)-4-benzyloxy-6-methylphenyl]-3-(2,6-dimethylphenylamino)- imidazo[1,2-a]pyridine “A174”2-[2-(Aminocarbonylmethoxy)phenyl]-3-(2-methyl-6-ethylphenylamino)-6-fluoroimidazo-[1,2-a]pyridine “A175”2-[2-(Aminocarbonylmethoxy)-6-hydroxyphenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo-[1,2-a]pyridine “A176”2-[2-(Aminocarbonylmethoxy)-6-hydroxyphenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]-pyridine “A177”2-[2-(Aminocarbonylmethoxy)-4-(tetra-hydropyran-2-yloxy)-6-methylphenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]-pyridine “A178”2-[2-(Aminocarbonylmethoxy)-4-(amino-carbonylmethoxy)-6-methylphenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]-pyridine “A179”2-[2-(Aminocarbonylmethoxy)-4-nitrophenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A180”2-{1-[3-(2,6-Dimethylphenylamino)-6-fluoro-imidazo[1,2-a]pyridin-2-yl]naphthalen-2-yloxy}-acetamide  

“A181” 2-{1-[3-(2,6-Dimethylphenylamino)imidazo-[1,2-a]pyridin-2-yl]naphthalen-2-yloxy}acetamide “A182”2-[2-(Aminocarbonylmethoxy)-4-(tetra-hydropyran-2-yloxy)-6-ethylphenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]-pyridine “A183”2-[2-(Aminocarbonylmethoxy)-5- (methoxycarbonylmethyl)phenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A184”2-[2-(Aminocarbonylmethoxy)-4-(2-methoxy-ethoxy)-6-methylphenyl]-3-(2,6-dimethylphenyl-amino)-6-fluoroimidazo[1,2-a]pyridine “A185”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-ethylphenyl]-3-(2,6-dimethylphenylamino)-6- fluoroimidazo[1,2-a]pyridine“A186” 2-[2-(Aminocarbonylmethoxy)-4-(2-hydroxy-ethoxy)-6-methylphenyl]-3-(2,6-dimethylphenyl-amino)-6-fluoroimidazo[1,2-a]pyridine “A187”2-[2-(Aminocarbonylmethoxy)-4-(2-methoxy-ethoxy)-6-ethylphenyl]-3-(2,6-dimethylphenyl-amino)-6-fluoroimidazo[1,2-a]pyridine “A188”2-[2-(Aminocarbonylmethoxy)-3,4-dimethoxy-phenyl]-3-(2,6-dimethylphenylamino)-6-fluoro- imidazo[1,2-a]pyridine“A189” 2-[2-(Aminocarbonylmethoxy)-4,5-dimethoxy-phenyl]-3-(2,6-dimethylphenylamino)-6-fluoro- imidazo[1,2-a]pyridine“A190” 2-[2-(Aminocarbonylmethoxy)-4-(2-oxo-1,3-dioxolan-4-yloxy)-6-methylphenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]-pyridine “A191”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methylphenyl]-3-(2,6-dimethylphenylamino)-8- aminoimidazo[1,2-a]pyridine“A192” 2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-ethylphenyl]-3-(2,6-dimethylphenylamino)-8- aminoimidazo[1,2-a]pyridine“A193” 2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methylphenyl]-3-(2,6-dimethylphenylamino)-8-hydroxyimidazo[1,2-a]pyridine “A194”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-ethylphenyl]-3-(2,6-dimethylphenylamino)-8-hydroxyimidazo[1,2-a]pyridine “A195”2-[2-(Aminocarbonylmethoxy)-4-(2-hydroxy-ethoxy)-6-ethylphenyl]-3-(2,6-dimethylphenyl-amino)-6-fluoroimidazo[1,2-a]pyridine “A196”2-[2-(Aminocarbonylmethoxy)-4-ethoxy-6-ethyl-phenyl]-3-(2,6-dimethylphenylamino)-6-fluoro- imidazo[1,2-a]pyridine“A197” 2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-chlorophenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridine “A198”2-[2-(Aminocarbonylmethoxy)-4-(2-oxo-1,3-dioxolan-4-yloxy)-6-ethylphenyl]-3-(2,6-dimethyl-phenylamino)-6-fluoroimidazo[1,2-a]pyridine  

“A199” 2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methoxyphenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridine “A200”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methoxyphenyl]-3-(2,6-dimethyl-4-fluorophenyl-amino)-6-fluoroimidazo[1,2-a]pyridine “A201”2-[2-(Aminocarbonylmethoxy)-3,4-dimethoxy-6-methylphenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridine “A202”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-ethylphenyl]-3-(2,6-dimethylphenylamino)- imidazo[1,2-a]pyridine “A203”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-ethylphenyl]-3-(2,6-dimethyl-4-fluorophenyl-amino)imidazo[1,2-a]pyridine “A204”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methylphenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridine “A205”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methylphenyl]-3-(2,6-dichlorophenylamino)-6-fluoroimidazo[1,2-a]pyridine “A206”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methylphenyl]-3-(2,6-dimethylphenylamino)-5-methylimidazo[1,2-a]pyridine “A207”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methylphenyl]-3-(2,6-dimethylphenylamino)-5- aminoimidazo[1,2-a]pyridine“A208” 2-[2-(Aminocarbonylmethoxy)-4-(2,3-dihydroxy-propoxy)-6-methylphenyl]-3-(2,6-dimethylphenyl-amino)-6-fluoroimidazo[1,2-a]pyridine  

“A209” 2-[2-(Aminocarbonylmethoxy)phenyl]-3-(2,6-dimethylphenylamino)-6-cyanoimidazo[1,2-a]-pyridine “A210”2-[2-(Aminocarbonylmethoxy)phenyl]-3-(2,6-dimethylphenylamino)-7-cyanoimidazo[1,2-a]-pyridine “A211”2-[2-(Aminocarbonylmethoxy)-4-methoxy-phenyl]-3-(2,6-dimethylphenylamino)-6-fluoro- imidazo[1,2-a]pyridine“A212” 2-[2-(Aminocarbonylmethoxy)-4-methoxy-phenyl]-3-(2,6-dimethyl-4-fluorophenylamino)-6-fluoroimidazo[1,2-a]pyridine “A213”2-[2-(Aminocarbonylmethoxy)-4-dimethyl-sulfamoyloxyphenyl]-3-(2,6-dimethylphenyl-amino)-6-fluoroimidazo[1,2-a]pyridine  

“A214” 2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methylphenyl]-3-(2-methoxy-6-methylphenyl-amino)-6-fluoroimidazo[1,2-a]pyridine “A215”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-ethylphenyl]-3-(2-methoxy-6-methylphenyl-amino)-6-fluoroimidazo[1,2-a]pyridine “A216”2-[2-(Aminocarbonylmethoxy)-4-(2,3-dihydroxy-propoxy)-6-ethylphenyl]-3-(2,6-dimethylphenyl-amino)-6-fluoroimidazo[1,2-a]pyridine “A217”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-ethylphenyl]-3-(3-chloro-2,6-dimethylphenyl-amino)-6-fluoroimidazo[1,2-a]pyridine “A218”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methylphenyl]-3-(3-chloro-2,6-dimethylphenyl-amino)-6-fluoroimidazo[1,2-a]pyridine “A219”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methylphenyl]-3-(2,6-difluorophenylamino)-6-fluoroimidazo[1,2-a]pyridine “A220”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-ethylphenyl]-3-(2,6-difluorophenylamino)-6- fluoroimidazo[1,2-a]pyridine“A221” 2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-ethylphenyl]-3-(2,6-dimethylphenylamino)-6,8-difluoroimidazo[1,2-a]pyridine “A222”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methylphenyl]-3-(4-chloro-2,6-dimethylphenyl-amino)-6-fluoroimidazo[1,2-a]pyridine “A223”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-ethylphenyl]-3-(2,6-dimethylphenylamino)-6-carboxyimidazo[1,2-a]pyridine “A224”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methylphenyl]-3-(4-fluoro-2,6-dichlorophenyl-amino)imidazo[1,2-a]pyridine “A225”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methylphenyl]-3-(4-fluoro-2,6-dichlorophenyl-amino)-6,8-difluoroimidazo[1,2-a]pyridine “A226”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methylphenyl]-3-(2,6-dichlorophenylamino)-6,8-difluoroimidazo[1,2-a]pyridine “A227”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-ethylphenyl]-3-(2,6-dimethylphenylamino)-5-amino-6,8-difluoroimidazo[1,2-a]pyridine “A228”2-[2-(Aminocarbonylmethoxy)-4-dimethyl-sulfamoyloxy-6-ethylphenyl]-3-(2,6-dimethyl-phenylamino)-6-fluoroimidazo[1,2-a]pyridine “A229”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methylphenyl]-3-(2,4-difluorophenylamino)-6-fluoroimidazo[1,2-a]pyridine “A230”2-[2-(Aminocarbonylmethoxy)-4-(amino-carbonylmethoxy)-6-ethylphenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]-pyridine “A231”2-[2-(Aminocarbonylmethoxy)-5-chloro-4-methoxy-6-methylphenyl]-3-(2,6-dimethylphenyl-amino)-6-fluoroimidazo[1,2-a]pyridine “A232”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methylphenyl]-3-(2-methyl-6-nitrophenylamino)-6-fluoroimidazo[1,2-a]pyridine “A233”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methylphenyl]-3-(2,6-dibromophenylamino)-6- fluoroimidazo[1,2-a]pyridine“A234” 2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methylphenyl]-3-(2,6-dimethyl-4-fluorophenyl-amino)-6-fluoroimidazo[1,2-a]pyridine “A235”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-ethylphenyl]-3-(2,6-dimethyl-4-fluorophenyl-amino)-6-fluoroimidazo[1,2-a]pyridine “A236”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methylphenyl]-3-(2-methyl-6-trifluoromethyl-phenylamino)-6-fluoroimidazo[1,2-a]pyridine “A237”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methylphenyl]-3-(2,6-dimethylphenylamino)-6,8-difluoroimidazo[1,2-a]pyridine “A238”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methylphenyl]-3-(2,6-dibromo-4-fluorophenyl-amino)-6-fluoroimidazo[1,2-a]pyridine “A239”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methylphenyl]-3-(2,6-dibromo-4-methylphenyl-amino)-6-fluoroimidazo[1,2-a]pyridine “A240”2-[2-(Aminocarbonylmethoxy)-6-ethylphenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo-[1,2-a]pyridine “A241”2-[2-(Aminocarbonylmethoxy)-6-ethylphenyl]-3-(2,6-dichlorophenylamino)-6-fluoroimidazo-[1,2-a]pyridine “A242”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methylphenyl]-3-(2-fluoro-6-trifluoromethyl-phenylamino)-6-fluoroimidazo[1,2-a]pyridine “A243”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methylphenyl]-3-(2-fluoro-6-bromophenylamino)-6-fluoroimidazo[1,2-a]pyridine “A244”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methylphenyl]-3-(2,4,6-trifluorophenylamino)-6-fluoroimidazo[1,2-a]pyridine “A245”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-ethylphenyl]-3-(2,6-dimethyl-4-methoxycarbonyl-phenylamino)-6-fluoroimidazo[1,2-a]pyridine “A246”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methylphenyl]-3-(2-methyl-6-methoxycarbonyl-phenylamino)-6-fluoroimidazo[1,2-a]pyridine “A247”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-ethylphenyl]-3-(2-methyl-6-trifluoromethylphenyl-amino)-6-fluoroimidazo[1,2-a]pyridine “A248”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methylphenyl]-3-(2-fluoro-6-chlorophenylamino)-6-fluoroimidazo[1,2-a]pyridine “A249”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methylphenyl]-3-(2,5-dimethyl-4,6-dibromophenylamino)-6-fluoroimidazo[1,2-a]-pyridine “A250”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methylphenyl]-3-(2,4-dimethyl-6-nitrophenyl-amino)-6-fluoroimidazo[1,2-a]pyridine “A251”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methylphenyl]-3-(2,6-dimethyl-4-fluorophenyl-amino)-6,8-difluoroimidazo[1,2-a]pyridine “A252”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methylphenyl]-3-(2,6-difluoro-4-bromophenyl-amino)-6-fluoroimidazo[1,2-a]pyridine “A253”2-[2-(Aminocarbonylmethoxy)-6-methylphenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo-[1,2-a]pyridine “A254”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methylphenyl]-3-(2,6-dimethyl-4-nitrophenyl-amino)-6-fluoroimidazo[1,2-a]pyridine “A255”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-ethylphenyl]-3-(2,6-dimethyl-4-fluorophenyl-amino)-6,8-difluoroimidazo[1,2-a]pyridine “A256”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methylphenyl]-3-(2-chloro-6-methylphenyl-amino)-6-fluoroimidazo[1,2-a]pyridine “A257”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-ethylphenyl]-3-(2-chloro-6-methylphenylamino)-6-fluoroimidazo[1,2-a]pyridine

Pharmacological Data

Affinity to Receptors

TABLE 1 Compound No. SGLT₁-IC₅₀ SGLT₂-IC₅₀ “A1” B A “A2” B A “A3” B A“A4” C A “A5” C A “A6” C A “A7” C B “A8” C B “A9” C A “A10” B A “A11” BA “A12” B “A13” B A “A14” C A “A15” B A “A16” B A “A17” C A “A165” C A“A166” C A “A167” C A “A168” C A “A169” B A “A170” B A “A171” C A “A172”C A “A173” C C “A174” C A “A175” C A “A176” C B “A119” — B “A177” C A“A102” B A “A178” C A “A179” C A “A180” B A “A181” B A “A182” C A “A183”C B “A184” C A “A185” B A “A186” C A “A187” C a “A188” C b “A189” — B“A190” C A “A191” C A “A192” C A “A193” — B “A194” C B “A195” C A “A196”C A “A197” C A “A198” B A “A199” C A “A200” C A “A201” C B “A202” B A“A203” B A “A204” B A “A205” B A “A206” C A “A207” C A “A208” C A “A209”C B “A210” C C “A211” C A “A212” C A “A213” C A “A214” C A “A215” C A“A216” C A “A217” B A “A218” B A “A219” B A “A220” B A “A221” B A “A222”B A “A223” — B “A224” B A “A225” B A “A226” B A “A227” B A “A228” C A“A229” C B “A230” C A “A231” B A “A232” B A “A233” C A “A234” B A “A235”B A “A236” B A “A237” B A “A238” B A “A239” A A “A240” B A “A241” A A“A242” B A “A243” B A “A244” B A “A245” C B “A246” C B “A247” C A “A248”C A “A249” B B “A250” C A “A251” B A “A252” B B “A253” “A254” C A “A255”B A “A256” B A “A257” B A IC₅₀: 10 nM-1 μM = A 1 μM-10 μM = B >10 μM = C

The following examples relate to pharmaceutical compositions:

EXAMPLE A Injection Vials

A solution of 100 g of an active ingredient of the formula I and 5 g ofdisodium hydrogenphosphate in 3 I of bidistilled water is adjusted to pH6.5 using 2 N hydrochloric acid, sterile filtered, transferred intoinjection vials, lyophilised under sterile conditions and sealed understerile conditions. Each injection vial contains 5 mg of activeingredient.

EXAMPLE B Suppositories

A mixture of 20 g of an active ingredient of the formula I with 100 g ofsoya lecithin and 1400 g of cocoa butter is melted, poured into mouldsand allowed to cool. Each suppository contains 20 mg of activeingredient.

EXAMPLE C Solution

A solution is prepared from 1 g of an active ingredient of the formulaI, 9.38 g of NaH₂PO₄.2H₂O, 28.48 g of Na₂HPO₄.12H₂O and 0.1 g ofbenzalkonium chloride in 940 ml of bidistilled water. The pH is adjustedto 6.8, and the solution is made up to 1 l and sterilised byirradiation. This solution can be used in the form of eye drops.

EXAMPLE D Ointment

500 mg of an active ingredient of the formula I are mixed with 99.5 g ofVaseline under aseptic conditions.

EXAMPLE E Tablets

A mixture of 1 kg of active ingredient of the formula I, 4 kg oflactose, 1.2 kg of potato starch, 0.2 kg of talc and 0.1 kg of magnesiumstearate is pressed to give tablets in a conventional manner in such away that each tablet contains 10 mg of active ingredient.

EXAMPLE F Coated Tablets

Tablets are pressed analogously to Example E and subsequently coated ina conventional manner with a coating of sucrose, potato starch, talc,tragacanth and dye.

EXAMPLE G Capsules

2 kg of active ingredient of the formula I are introduced into hardgelatine capsules in a conventional manner in such a way that eachcapsule contains 20 mg of the active ingredient.

EXAMPLE H Ampoules

A solution of 1 kg of active ingredient of the formula I in 60 l ofbidistilled water is sterile filtered, transferred into ampoules,lyophilised under sterile conditions and sealed under sterileconditions. Each ampoule contains 10 mg of active ingredient.

1. Compounds of the formula I

in which R, R′ each, independently of one another, denote A, OA, Hal,NO₂ or COOA, R¹, R^(1′) each, independently of one another, denote H, A,F, Cl, NH₂, OH, CN or COOH, R^(1″) denotes H or NH₂, R², R^(2′) each,independently of one another, denote H, Hal, A, OH, OA, CN, NO₂,NR⁴R^(4′), CH₂NR⁴R^(4′), O(CH₂)_(m)NR⁴R^(4′), O(CH₂)_(m)OR⁴,NH(CH₂)_(m)NR⁴R^(4′), O(C═O)(CH₂)_(m)NR⁴R^(4′),NH(C═O)(CH₂)_(m)NR⁴R^(4′), CH₂O(CH₂)_(m)NR⁴R^(4′), CH₂OR⁴,(CH₂)_(m)COOR⁴, OSO₂A, OHet, O(CH₂)_(m)CONR⁴R^(4′), O(CH₂)_(m)Ar,O(CH₂)_(m)CH(OH)(CH₂)_(m)OH or OSO₂NR⁴R^(4′), R² and R^(2′) togetheralso denote —CH═CH—CH═CH—, R^(2″) denotes H, A, Hal, OH or OA, R³,R^(3′) each, independently of one another, denote H, A, Hal, NO₂ orCOOA, R⁴, R^(4′) each, independently of one another, denote H or A, X, Yeach, independently of one another, denote O, NH, CH₂ or are absent, Adenotes unbranched or branched alkyl having 1-10 C atoms, in which 1-7 Hatoms may be replaced by F, or cycloalkyl having 3-7 C atoms, Hetdenotes a monocyclic saturated heterocycle having 1 to 2 N, O and/or Satoms, which may be mono- or disubstituted by A, Hal, OA, OH and/or ═O(carbonyl oxygen), Ar denotes phenyl which is unsubstituted or mono-,di-, tri- or tetra-substituted by A, Hal, OA and/or OH, Hal denotes F,Cl, Br or I, m denotes 1, 2 or 3, n denotes 0, 1 or 2, andpharmaceutically usable derivatives, solvates, salts and stereoisomersthereof, including mixtures thereof in all ratios.
 2. Compoundsaccording to claim 1 in which A denotes unbranched or branched alkylhaving 1, 2, 3, 4, 5 or 6 C atoms, in which 1-5 H atoms may be replacedby F, and pharmaceutically usable derivatives, solvates, salts andstereoisomers thereof, including mixtures thereof in all ratios. 3.Compounds according to claim 1 in which R¹ denotes H, A, F, Cl, NH₂, OH,CN or COOH, R^(1′) denotes H, and pharmaceutically usable derivatives,solvates, salts and stereoisomers thereof, including mixtures thereof inall ratios.
 4. Compounds according to claim 1 in which R⁴, R^(4′) each,independently of one another, denote H or CH₃, and pharmaceuticallyusable derivatives, solvates, salts and stereoisomers thereof, includingmixtures thereof in all ratios.
 5. Compounds according to claim 1 inwhich Het denotes tetrahydrofuranyl, tetrahydropyranyl, dioxolanyl,pyrrolidinyl, piperidinyl, morpholinyl or piperazinyl, each of which mayalso be monosubstituted by ═O (carbonyl oxygen), and pharmaceuticallyusable derivatives, solvates, salts and stereoisomers thereof, includingmixtures thereof in all ratios.
 6. Compounds according to claim 1 inwhich Ar denotes phenyl, and pharmaceutically usable derivatives,solvates, salts and stereoisomers thereof, including mixtures thereof inall ratios.
 7. Compounds according to claim 1 of the formula Ia

in which R, R′ each, independently of one another, denote A, OA, Hal,NO₂ or COOA, R¹, R^(1′) each, independently of one another, denote H, A,F, Cl, NH₂, OH, CN or COOA, R^(1″) denotes H or NH₂, R², R^(2′) each,independently of one another, denote H, Hal, A, OH, OA, CN, NO₂,NR⁴R^(4′), CH₂NR⁴R^(4′), O(CH₂)_(m)NR⁴R^(4′), O(CH₂)_(m)OR⁴,NH(CH₂)_(m)NR⁴R^(4′), O(C═O)(CH₂)_(m)NR⁴R^(4′),NH(C═O)(CH₂)_(m)NR⁴R^(4′), CH₂O(CH₂)_(m)NR⁴R^(4′), CH₂OR⁴,(CH₂)_(m)COOR⁴, OSO₂A, OHet, O(CH₂)_(m)CONR⁴R^(4′), O(CH₂)_(m)Ar,O(CH₂)_(m)CH(OH)(CH₂)_(m)OH or OSO₂NR⁴R^(4′), R² and R^(2′) togetheralso denote —CH═CH—CH═CH—, R^(2″) denotes H, A, Hal, OH or OA, R³,R^(3′) each, independently of one another, denote H, A, Hal, NO₂ orCOOA, R⁴, R^(4′) each, independently of one another, denote H or A, Adenotes unbranched or branched alkyl having 1, 2, 3, 4, 5 or 6 C atoms,in which 1-5 H atoms may be replaced by F, Het denotestetrahydrofuranyl, tetrahydropyranyl, dioxolanyl, pyrrolidinyl,piperidinyl, morpholinyl or piperazinyl, each of which may also bemonosubstituted by ═O (carbonyl oxygen), Ar denotes phenyl, Hal denotesF, Cl, Br or I, m denotes 1, 2 or 3, n denotes 0, 1 or 2, andpharmaceutically usable derivatives, solvates, salts and stereoisomersthereof, including mixtures thereof in all ratios.
 8. Compoundsaccording to claim 1 selected from the group No. Name and/or structure“A1” 2-[2-(Aminocarbonylmethoxy)-6-methoxyphenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridine “A2”2-[2-(Aminocarbonylmethoxy)-6-methylphenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridine “A3”2-[2-(Aminocarbonylmethoxy)-6-chlorophenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridine “A4”2-[2-(Aminocarbonylmethoxy)phenyl]-3-(2,6-dimethylphenyl-amino)imidazo[1,2-a]pyridine “A5”2-[2-(Aminocarbonylmethoxy)phenyl]-3-(2,6-dichlorophenyl-amino)imidazo[1,2-a]pyridine “A6”2-[2-(Aminocarbonylmethoxy)phenyl]-3-(2-chloro-6-methyl-phenylamino)imidazo[1,2-a]pyridine “A7”2-[2-(Aminocarbonylmethoxy)phenyl]-3-(2-isopropyl-6-methylphenylamino)imidazo[1,2-a]pyridine “A8”2-[2-(Aminocarbonylmethoxy)phenyl]-3-(2,6-dimethylphenyl-amino)-8-methylimidazo[1,2-a]pyridine “A9”2-[2-(Aminocarbonylmethoxy)phenyl]-3-(2,6-dimethylphenyl-amino)-5-methylimidazo[1,2-a]pyridine “A10”2-[2-(Aminocarbonylmethoxy)phenyl]-3-(2-chloro-6-methyl-phenylamino)-5-methylimidazo[1,2-a]pyridine “A11”2-[2-(Aminocarbonylmethoxy)phenyl]-3-(2,6-dichlorophenyl-amino)-5-methylimidazo[1,2-a]pyridine “A12”2-[2-(Aminocarbonylmethoxy)phenyl]-3-(2,6-dimethylphenyl-amino)-5-chloroimidazo[1,2-a]pyridine “A13”2-[2-(Aminocarbonylmethoxy)phenyl]-3-(2,6-dimethylphenyl-amino)-5-ethylimidazo[1,2-a]pyridine “A14”2-[2-(Aminocarbonylmethoxy)-4-methoxyphenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A15”2-[2-(Aminocarbonylmethoxy)-4-methoxyphenyl]-3-(2-chloro-6-methylphenylamino)imidazo[1,2-a]pyridine “A16”2-[2-(Aminocarbonylmethoxy)-4-methoxyphenyl]-3-(2,6-dichlorophenylamino)imidazo[1,2-a]pyridine “A17”2-[2-(Aminocarbonylmethoxy)-4-methylphenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A18”2-[2-(Aminocarbonylmethoxy)-5-methoxyphenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A19”2-[2-(Aminocarbonylmethoxy)-5-methylphenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A20”2-[2-(Aminocarbonylmethoxy)-6-methylphenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A21”2-[2-(Aminocarbonylmethoxy)-6-chlorophenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A22”2-[2-(Aminocarbonylmethoxy)-6-methoxyphenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A23”2-[2-(Aminocarbonylmethoxy)-6-methoxyphenyl]-3-(2-chloro-6-methylphenylamino)imidazo[1,2-a]pyridine “A24”2-[2-(Aminocarbonylmethoxy)-6-methoxyphenyl]-3-(2,6-dichlorophenylamino)imidazo[1,2-a]pyridine “A25”2-[2-(Aminocarbonylmethoxy)phenyl]-3-(2,6-dimethylphenyl-amino)-6-fluoroimidazo[1,2-a]pyridine “A26”2-[2-(Aminocarbonylmethoxy)phenyl]-3-(2,6-dimethylphenyl-amino)-8-fluoroimidazo[1,2-a]pyridine “A27”2-[2-(Aminocarbonylmethoxy)-3-fluorophenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A28”2-[2-(Aminocarbonylmethoxy)-4-fluorophenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A29”2-[2-(Aminocarbonylmethoxy)phenyl]-3-(2,6-dimethylphenyl-amino)-5-fluoroimidazo[1,2-a]pyridine “A30”2-[2-(Aminocarbonylmethoxy)phenyl]-3-(2,6-dimethylphenyl-amino)-6,8-difluoroimidazo[1,2-a]pyridine “A31”2-[2-(Aminocarbonylmethoxy)-5-fluorophenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A32”2-[2-(Aminocarbonylmethoxy)-6-fluorophenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A33”2-[2-(Aminocarbonylmethoxy)-6-fluorophenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridine “A34”2-[2-(Aminocarbonylmethoxy)-4-fluorophenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridine “A35”2-[2-(Aminocarbonylmethoxy)-4-fluorophenyl]-3-(2,6-dimethylphenylamino)-5-fluoroimidazo[1,2-a]pyridine “A36”2-[2-(Aminocarbonylmethoxy)-6-methoxyphenyl]-3-(2,6-dimethylphenylamino)-5-fluoroimidazo[1,2-a]pyridine “A37”2-[2-(Aminocarbonylmethoxy)-6-methoxyphenyl]-3-(2,6-dimethylphenylamino)-6,8-difluoroimidazo[1,2-a]pyridine “A38”2-[2-(Aminocarbonylmethoxy)phenyl]-3-(2-ethyl-6-methyl-phenylamino)imidazo[1,2-a]pyridine “A39”2-[2-(Aminocarbonylmethoxy)-6-methoxyphenyl]-3-(2-ethyl-6-methylphenylamino)imidazo[1,2-a]pyridine “A40”2-[2-(Aminocarbonylmethoxy)phenyl]-3-(2,6-diethylphenyl-amino)imidazo[1,2-a]pyridine “A41”2-[2-(Aminocarbonylmethoxy)-6-methoxyphenyl]-3-(2,6-diethylphenylamino)imidazo[1,2-a]pyridine “A42”2-[2-(Aminocarbonylmethoxy)phenyl]-3-(2,4,6-trimethyl-phenylamino)imidazo[1,2-a]pyridine “A43”2-[2-(Aminocarbonylmethoxy)phenyl]-3-(2,4,6-trimethyl-phenylamino)-6-fluoroimidazo[1,2-a]pyridine “A44”2-[2-(Aminocarbonylmethoxy)phenyl]-3-(2,4,6-trimethyl-phenylamino)-5-fluoroimidazo[1,2-a]pyridine “A45”2-[2-(Aminocarbonylmethoxy)-6-methoxyphenyl]-3-(2,4,6-trimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridine “A46”2-[2-(Aminocarbonylmethoxy)-6-fluorophenyl]-3-(2,6-dimethyl-4-fluorophenylamino)-6-fluoroimidazo[1,2-a]- pyridine “A47”2-[2-(Aminocarbonylmethoxy)phenyl]-3-(2,6-dimethyl-4-fluorophenylamino)imidazo[1,2-a]pyridine “A48”2-[2-(Aminocarbonylmethoxy)-6-methoxyphenyl]-3-(2,6-dimethylphenylamino)-8-fluoroimidazo[1,2-a]pyridine “A49”2-[2-(Aminocarbonylmethoxy)phenyl]-3-(2,6-dimethyl-4-fluorophenylamino)-6-fluoroimidazo[1,2-a]pyridine “A50”2-[2-(Aminocarbonylmethoxy)phenyl]-3-(2-ethyl-6-methyl-phenylamino)-6-fluoroimidazo[1,2-a]pyridine “A51”2-[2-(Aminocarbonylmethoxy)phenyl]-3-(2-ethyl-6-methyl-phenylamino)-6,8-difluoroimidazo[1,2-a]pyridine “A52”2-[2-(Aminocarbonylmethoxy)-6-methylphenyl]-3-(2,6-dimethylphenylamino)-8-fluoroimidazo[1,2-a]pyridine “A53”2-[2-(Aminocarbonylmethoxy)-6-methylphenyl]-3-(2,6-dimethylphenylamino)-6,8-difluoroimidazo[1,2-a]pyridine “A54”2-[2-(Aminocarbonylmethoxy)-4-chlorophenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A55”2-[2-(Aminocarbonylmethoxy)-6-methylphenyl]-3-(2-ethyl-6-methylphenylamino)-6-fluoroimidazo[1,2-a]pyridine “A56”2-[2-(Aminocarbonylmethoxy)-4-chlorophenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridine “A57”2-[2-(Aminocarbonylmethoxy)phenyl]-3-(2,6-dimethylphenyl-amino)-6,8-difluoroimidazo[1,2-a]pyridine “A58”2-[2-(Aminocarbonylmethoxy)-4-fluorophenyl]-3-(2,6-dimethyl-4-fluorophenylamino)-6-fluoroimidazo[1,2-a]- pyridine “A59”2-[2-(Aminocarbonylmethoxy)-6-methylphenyl]-3-(2,6-dimethyl-4-fluorophenylamino)-6-fluoroimidazo[1,2-a]- pyridine “A60”2-[2-(Aminocarbonylmethoxy)-4-cyanophenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridine “A61”2-[2-(Aminocarbonylmethylamino)phenyl]-3-(2,6-dimethyl-phenylamino)imidazo[1,2-a]pyridine

“A62” 2-[2-(Ureidomethyl)phenyl]-3-(2,6-dimethylphenylamino)-imidazo[1,2-a]pyridine

“A63” 2-[2-(Aminocarbonylmethylamino)phenyl]-3-(2,6-dimethyl-phenylamino)-6-fluoroimidazo[1,2-a]pyridine “A64”2-[2-(Ureidomethyl)phenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridine “A65”2-[2-(Aminocarbonylmethylamino)phenyl]-3-(2,6-dimethyl-phenylamino)-6,8-difluoroimidazo[1,2-a]pyridine “A66”2-[2-(Ureidomethyl)phenyl]-3-(2,6-dimethylphenylamino)-6,8-difluoroimidazo[1,2-a]pyridine “A67”2-[2-(Aminocarbonylmethoxy)-5-fluorophenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A68”2-[2-(Aminocarbonylmethoxy)-5-chlorophenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A69”2-[2-(Aminocarbonylmethoxy)-5-nitrophenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A70”2-[2-(Aminocarbonylmethoxy)-5-aminophenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A71”2-[2-(Aminocarbonylmethoxy)-5-fluorophenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridine “A72”2-[2-(Aminocarbonylmethoxy)-5-chlorophenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridine “A73”2-[2-(Aminocarbonylmethoxy)-5-nitrophenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridine “A74”2-[2-(Aminocarbonylmethoxy)-5-aminophenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridine “A75”2-[2-(Aminocarbonylmethoxy)-4-hydroxyphenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A76”2-[2-(Aminocarbonylmethoxy)-4,6-dimethylphenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A77”2-[2-(Aminocarbonylmethoxy)-4-bromophenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A78”2-[2-(Aminocarbonylmethoxy)-4-cyanophenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A79”2-[2-(Aminocarbonylmethoxy)-4-hydroxyphenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridine “A80”2-[2-(Aminocarbonylmethoxy)-4-bromophenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridine “A81”2-[2-(Aminocarbonylmethoxy)-4-chlorophenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridine “A82”2-[2-(Aminocarbonylmethoxy)-4-methylphenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridine “A83”2-[2-(Aminocarbonyloxy)phenyl]-3-(2,6-dimethylphenyl-amino)imidazo[1,2-a]pyridine

“A84” 2-[2-(Aminocarbonyloxymethy)phenyl]-3-(2,6-dimethyl-phenylamino)imidazo[1,2-a]pyridine “A85”2-[2-(Methylaminocarbonylmethoxy)phenyl]-3-(2,6-dimethyl-phenylamino)imidazo[1,2-a]pyridine “A86”2-[2-(Dimethylaminocarbonylmethoxy)phenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A87”2-{2-[2-(Aminocarbonyl)ethoxy]phenyl}-3-(2,6-dimethyl-phenylamino)imidazo[1,2-a]pyridine “A88”2-[2-(Aminocarbonyloxy)phenyl]-3-(2,6-dimethylphenyl-amino)-6-fluoroimidazo[1,2-a]pyridine “A89”2-[2-(Aminocarbonyloxymethyl)phenyl]-3-(2,6-dimethyl-phenylamino)-6-fluoroimidazo[1,2-a]pyridine “A90”2-[2-(Methylaminocarbonylmethoxy)phenyl]-3-(2,6-dimethyl-phenylamino)-6-fluoroimidazo[1,2-a]pyridine “A91”2-[2-(Dimethylaminocarbonylmethoxy)phenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridine “A92”2-{2-[2-(Aminocarbonyl)ethoxy]phenyl}-3-(2,6-dimethyl-phenylamino)-6-fluoroimidazo[1,2-a]pyridine “A93”2-[2-(Aminocarbonylmethoxy)-6-cyano-4-hydroxyphenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A94”2-[2-(Aminocarbonylmethoxy)-6-chloro-4-hydroxyphenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridine “A95”2-[2-(Aminocarbonylmethoxy)-6-bromo-4-hydroxyphenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A96”2-[2-(Aminocarbonylmethoxy)-6-methyl-4-hydroxyphenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A97”2-[2-(Aminocarbonylmethoxy)-6-ethyl-4-hydroxyphenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A98”2-[2-(Aminocarbonylmethoxy)-6-cyano-4-hydroxyphenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridine “A99”2-[2-(Aminocarbonylmethoxy)-6-chloro-4-hydroxyphenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridine “A100”2-[2-(Aminocarbonylmethoxy)-6-bromo-4-hydroxyphenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridine “A101”2-[2-(Aminocarbonylmethoxy)-6-methyl-4-hydroxyphenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridine “A102”2-[2-(Aminocarbonylmethoxy)-6-ethyl-4-hydroxyphenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridine “A103”2-[2-(Aminocarbonylmethoxy)-6-methyl-4-(2-methyl-aminoacetoxy)phenyl]-3-(2,6-dimethylphenylamino)imidazo- [1,2-a]pyridine

“A104” 2-[2-(Aminocarbonylmethoxy)-6-methyl-4-(2-methyl-aminoacetoxy)phenyl]-3-(2,6-dimethylphenylamino)-6-fluoro-imidazo[1,2-a]pyridine “A105”2-[2-(Aminocarbonylmethoxy)-6-methyl-4-(2-methyl-aminoacetylamino)phenyl]-3-(2,6-dimethylphenylamino)-imidazo[1,2-a]pyridine

“A106” 2-[2-(Aminocarbonylmethoxy)-6-methyl-4-(2-methyl-aminoacetylamino)phenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridine “A107”2-[2-(Aminocarbonylmethoxy)-4-(2-methylaminoacetoxy)-phenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A108”2-[2-(Aminocarbonylmethoxy)-4-(2-methylaminoacetoxy)-phenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]- pyridine“A109” 2-[2-(Aminocarbonylmethoxy)-4-(2-methylaminoacetyl-amino)phenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]- pyridine “A110”2-[2-(Aminocarbonylmethoxy)-4-(2-methylaminoacetyl-amino)phenyl]-3-(2,6-dimethylphenylamino)-6-fluoro-imidazo[1,2-a]pyridine “A111”2-[2-(Aminocarbonylmethoxy)-4-(2-aminoethoxy)-6-chlorophenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]- pyridine

“A112” 2-[2-(Aminocarbonylmethoxy)-4-(2-methylaminoethoxy)-6-chlorophenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]- pyridine “A113”2-[2-(Aminocarbonylmethoxy)-4-(2-dimethylaminoethoxy)-6-chlorophenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]- pyridine “A114”2-[2-(Aminocarbonylmethoxy)-4-(2-aminoethoxy)-6-chlorophenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo-[1,2-a]pyridine “A115”2-[2-(Aminocarbonylmethoxy)-4-(2-methylaminoethoxy)-6-chlorophenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo-[1,2-a]pyridine “A116”2-[2-(Aminocarbonylmethoxy)-4-(2-dimethylaminoethoxy)-6-chlorophenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo-[1,2-a]pyridine “A117”2-[2-(Aminocarbonylmethoxy)-4-(2-aminoethoxy)-6-methyl-phenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A118”2-[2-(Aminocarbonylmethoxy)-4-(2-methylaminoethoxy)-6-methylphenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]- pyridine “A119”2-[2-(Aminocarbonylmethoxy)-4-(2-dimethylaminoethoxy)-6-methylphenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]- pyridine “A120”2-[2-(Aminocarbonylmethoxy)-4-(2-aminoethoxy)-6-methyl-phenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]- pyridine“A121” 2-[2-(Aminocarbonylmethoxy)-4-(2-methylaminoethoxy)-6-methylphenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo-[1,2-a]pyridine “A122”2-[2-(Aminocarbonylmethoxy)-4-(2-dimethylaminoethoxy)-6-methylphenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo-[1,2-a]pyridine “A123”2-[2-(Aminocarbonylmethoxy)-6-bromophenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A124”2-[2-(Aminocarbonylmethoxy)-6-nitrophenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A125”2-[2-(Aminocarbonylmethoxy)-6-cyanophenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A126”2-[2-(Aminocarbonylmethoxy)-6-carboxyphenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A127”2-[2-(Aminocarbonylmethoxy)-6-hydroxymethylphenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A128”2-[2-(Aminocarbonylmethoxy)-6-bromophenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridine “A129”2-[2-(Aminocarbonylmethoxy)-6-nitrophenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridine “A130”2-[2-(Aminocarbonylmethoxy)-6-cyanophenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridine “A131”2-[2-(Aminocarbonylmethoxy)-6-carboxyphenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridine “A132”2-[2-(Aminocarbonylmethoxy)-6-hydroxymethylphenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridine “A133”2-[2-(Aminocarbonylmethoxy)-6-(2-methylamino-ethoxymethyl)phenyl]-3-(2,6-dimethylphenylamino)imidazo- [1,2-a]pyridine

“A134” 2-[2-(Aminocarbonylmethoxy)-6-(2-methylamino-ethoxymethyl)phenyl]-3-(2,6-dimethylphenylamino)-6-fluoro-imidazo[1,2-a]pyridine “A135”2-[2-(Aminocarbonylmethoxy)-6-(2-methylamino-ethoxymethyl)phenyl]-3-(2,6-dimethylphenylamino)-6,8-difluoroimidazo[1,2-a]pyridine “A136”2-[2-(Aminocarbonylmethoxy)-6-(2-methylaminoethoxy)-phenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A137”2-[2-(Aminocarbonylmethoxy)-6-aminophenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A138”2-[2-(Aminocarbonylmethoxy)-6-(2-methoxyethylamino)-phenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine

“A139” 2-[2-(Aminocarbonylmethoxy)-6-(2-hydroxyethylamino)-phenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A140”2-[2-(Aminocarbonylmethoxy)-6-(2-aminoethylamino)-phenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A141”2-[2-(Aminocarbonylmethoxy)-6-(2-methylaminoethylamino)-phenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A142”2-[2-(Aminocarbonylmethoxy)-6-aminophenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridine “A143”2-[2-(Aminocarbonylmethoxy)-6-(2-methoxyethylamino)-phenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]- pyridine“A144” 2-[2-(Aminocarbonylmethoxy)-6-(2-hydroxyethylamino)-phenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]- pyridine“A145” 2-[2-(Aminocarbonylmethoxy)-6-(2-aminoethylamino)-phenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]- pyridine“A146” 2-[2-(Aminocarbonylmethoxy)-6-(2-methylaminoethylamino)-phenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]- pyridine“A147” 2-[2-(Aminocarbonylmethoxy)-6-aminophenyl]-3-(2,6-dimethylphenylamino)-6,8-difluoroimidazo[1,2-a]pyridine “A148”2-[2-(Aminocarbonylmethoxy)-6-(2-methoxyethylamino)-phenyl]-3-(2,6-dimethylphenylamino)-6,8-difluoroimidazo- [1,2-a]pyridine“A149” 2-[2-(Aminocarbonylmethoxy)-6-(2-hydroxyethylamino)-phenyl]-3-(2,6-dimethylphenylamino)-6,8-difluoroimidazo- [1,2-a]pyridine“A150” 2-[2-(Aminocarbonylmethoxy)-6-(2-aminoethylamino)-phenyl]-3-(2,6-dimethylphenylamino)-6,8-difluoroimidazo- [1,2-a]pyridine“A151” 2-[2-(Aminocarbonylmethoxy)-6-(2-methylaminoethylamino)-phenyl]-3-(2,6-dimethylphenylamino)-6,8-difluoroimidazo- [1,2-a]pyridine“A152” 2-[2-(Aminocarbonylmethoxy)-4-(2-aminoethoxy)-6-bromophenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]- pyridine “A153”2-[2-(Aminocarbonylmethoxy)-4-(2-aminoethoxy)-6-cyanophenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]- pyridine “A154”2-[2-(Aminocarbonylmethoxy)-4-(2-aminoethoxy)-6-bromophenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo-[1,2-a]pyridine “A155” 2-[2-(Aminocarbonylmethoxy)-4-(2-aminoethoxy)-6-cyanophenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo-[1,2-a]pyridine “A156”2-[2-(Aminocarbonylmethoxy)-6-hydroxyphenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A157”2-[2-(Aminocarbonylmethoxy)-6-hydroxyphenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridine “A158”2-[2-(Aminocarbonylmethoxy)-6-(2-hydroxyethoxy)phenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A159”2-[2-(Aminocarbonylmethoxy)-6-(2-hydroxyethoxy)phenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridine “A160”2-[2-(Aminocarbonylmethoxy)-6-hydroxyphenyl]-3-(2,6-dimethylphenylamino)-6,8-difluoroimidazo[1,2-a]pyridine “A161”2-[2-(Aminocarbonylmethoxy)-6-propylphenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A162”2-[2-(Aminocarbonylmethoxy)-6-propylphenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridine “A163”2-[2-(Aminocarbonylmethoxy)-4-hydroxy-6-propylphenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A164”2-[2-(Aminocarbonylmethoxy)-4-hydroxy-6-propylphenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridine “A165”2-[2-(Aminocarbonylmethoxy)-4-methylsulfonyloxy-6-methylphenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]- pyridine

“A166” 2-[2-(Aminocarbonylmethoxy)-4-(tetrahydropyran-2-yloxy)-6-ethylphenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]- pyridine

“A167” 2-[2-(Aminocarbonylmethoxy)-4-(aminocarbonylmethoxy)-6-ethylphenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]- pyridine

“A168” 2-[2-(Aminocarbonylmethoxy)-4,6-dimethylphenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A169”2-[2-(Aminocarbonylmethoxy)-4,6-dimethylphenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridine “A170”2-[2-(Aminocarbonylmethoxy)-4-(aminocarbonylmethoxy)-6-methylphenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]- pyridine “A171”2-[2-(Aminocarbonylmethoxy)-4-hydroxy-6-methylphenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A172”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methylphenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A173”2-[2-(Aminocarbonylmethoxy)-4-benzyloxy-6-methylphenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A174”2-[2-(Aminocarbonylmethoxy)phenyl]-3-(2-methyl-6-ethyl-phenylamino)-6-fluoroimidazo[1,2-a]pyridine “A175”2-[2-(Aminocarbonylmethoxy)-6-hydroxyphenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridine “A176”2-[2-(Aminocarbonylmethoxy)-6-hydroxyphenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A177”2-[2-(Aminocarbonylmethoxy)-4-(tetrahydropyran-2-yloxy)-6-methylphenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo-[1,2-a]pyridine “A178”2-[2-(Aminocarbonylmethoxy)-4-(aminocarbonylmethoxy)-6-methylphenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo-[1,2-a]pyridine “A179”2-[2-(Aminocarbonylmethoxy)-4-nitrophenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A180”2-{1-[3-(2,6-Dimethylphenylamino)-6-fluoroimidazo[1,2-a]-pyridin-2-yl]naphthalen-2-yloxy}acetamide

“A181” 2-{1-[3-(2,6-Dimethylphenylamino)imidazo[1,2-a]pyridin-2-yl]naphthalen-2-yloxy}acetamide “A182”2-[2-(Aminocarbonylmethoxy)-4-(tetrahydropyran-2-yloxy)-6-ethylphenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo-[1,2-a]pyridine “A183”2-[2-(Aminocarbonylmethoxy)-5-(methoxycarbonylmethyl)-phenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A184”2-[2-(Aminocarbonylmethoxy)-4-(2-methoxyethoxy)-6-methylphenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo-[1,2-a]pyridine “A185”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-ethylphenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridine “A186”2-[2-(Aminocarbonylmethoxy)-4-(2-hydroxyethoxy)-6-methylphenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo-[1,2-a]pyridine “A187”2-[2-(Aminocarbonylmethoxy)-4-(2-methoxyethoxy)-6-ethyl-phenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]- pyridine“A188” 2-[2-(Aminocarbonylmethoxy)-3,4-dimethoxyphenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridine “A189”2-[2-(Aminocarbonylmethoxy)-4,5-dimethoxyphenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridine “A190”2-[2-(Aminocarbonylmethoxy)-4-(2-oxo-1,3dioxolan-4-yloxy)-6-methylphenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridine “A191”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methylphenyl]-3-(2,6-dimethylphenylamino)-8-aminoimidazo[1,2-a]pyridine “A192”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-ethylphenyl]-3-(2,6-dimethylphenylamino)-8-aminoimidazo[1,2-a]pyridine “A193”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methylphenyl]-3-(2,6-dimethylphenylamino)-8-hydroxyimidazo[1,2-a]- pyridine “A194”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-ethylphenyl]-3-(2,6-dimethylphenylamino)-8-hydroxyimidazo[1,2-a]pyridine “A195”2-[2-(Aminocarbonylmethoxy)-4-(2-hydroxyethoxy)-6-ethyl-phenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]- pyridine“A196” 2-[2-(Aminocarbonylmethoxy)-4-ethoxy-6-ethylphenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridine “A197”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-chlorophenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridine “A198”2-[2-(Aminocarbonylmethoxy)-4-(2-oxo-1,3-dioxolan-4-yloxy)-6-ethylphenyl]-3-(2,6-dimethylphenylamino)-6-fluoro-imidazo[1,2-a]pyridine

“A199” 2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methoxyphenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridine “A200”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methoxyphenyl]-3-(2,6-dimethyl-4-fluorophenylamino)-6-fluoroimidazo- [1,2-a]pyridine“A201” 2-[2-(Aminocarbonylmethoxy)-3,4-dimethoxy-6-methyl-phenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]- pyridine“A202” 2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-ethylphenyl]-3-(2,6-dimethylphenylamino)imidazo[1,2-a]pyridine “A203”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-ethylphenyl]-3-(2,6-dimethyl-4-fluorophenylamino)imidazo[1,2-a]pyridine “A204”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methylphenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridine “A205”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methylphenyl]-3-(2,6-dichlorophenylamino)-6-fluoroimidazo[1,2-a]pyridine “A206”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methylphenyl]-3-(2,6-dimethylphenylamino)-5-methylimidazo[1,2-a]pyridine “A207”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methylphenyl]-3-(2,6-dimethylphenylamino)-5-aminoimidazo[1,2-a]pyridine “A208”2-[2-(Aminocarbonylmethoxy)-4-(2,3-dihydroxypropoxy)-6-methylphenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo-[1,2-a]pyridine

“A209” 2-[2-(Aminocarbonylmethoxy)phenyl]-3-(2,6-dimethylphenyl-amino)-6-cyanoimidazo[1,2-a]pyridine “A210”2-[2-(Aminocarbonylmethoxy)phenyl]-3-(2,6-dimethylphenyl-amino)-7-cyanoimidazo[1,2-a]pyridine “A211”2-[2-(Aminocarbonylmethoxy)-4-methoxyphenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridine “A212”2-[2-(Aminocarbonylmethoxy)-4-methoxyphenyl]-3-(2,6-dimethyl-4-fluorophenylamino)-6-fluoroimidazo[1,2-a]- pyridine “A213”2-[2-(Aminocarbonylmethoxy)-4-dimethylsulfamoyloxy-phenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]- pyridine

“A214” 2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methylphenyl]-3-(2-methoxy-6-methylphenylamino)-6-fluoroimidazo[1,2-a]- pyridine“A215” 2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-ethylphenyl]-3-(2-methoxy-6-methylphenylamino)-6-fluoroimidazo[1,2-a]- pyridine “A216”2-[2-(Aminocarbonylmethoxy)-4-(2,3-dihydroxypropoxy)-6-ethylphenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo-[1,2-a]pyridine “A217”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-ethylphenyl]-3-(3-chloro-2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]- pyridine“A218” 2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methylphenyl]-3-(3-chloro-2,6-dimethylphenylamino)-6-fluoroimidazo- [1,2-a]pyridine“A219” 2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methylphenyl]-3-(2,6-difluorophenylamino)-6-fluoroimidazo[1,2-a]pyridine “A220”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-ethylphenyl]-3-(2,6-difluorophenylamino)-6-fluoroimidazo[1,2-a]pyridine “A221”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-ethylphenyl]-3-(2,6-dimethylphenylamino)-6,8-difluoroimidazo[1,2-a]- pyridine “A222”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methylphenyl]-3-(4-chloro-2,6-dimethylphenylamino)-6-fluoroimidazo- [1,2-a]pyridine“A223” 2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-ethylphenyl]-3-(2,6-dimethylphenylamino)-6-carboxyimidazo[1,2-a]pyridine “A224”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methylphenyl]-3-(4-fluoro-2,6-dichlorophenylamino)imidazo[1,2-a]pyridine “A225”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methylphenyl]-3-(4-fluoro-2,6-dichlorophenylamino)-6,8-difluoroimidazo-[1,2-a]pyridine “A226”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methylphenyl]-3-(2,6-dichlorophenylamino)-6,8-difluoroimidazo[1,2-a]- pyridine “A227”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-ethylphenyl]-3-(2,6-dimethylphenylamino)-5-amino-6,8-difluoroimidazo- [1,2-a]pyridine“A228” 2-[2-(Aminocarbonylmethoxy)-4-dimethylsulfamoyloxy-6-ethylphenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo-[1,2-a]pyridine “A229”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methylphenyl]-3-(2,4-difluorophenylamino)-6-fluoroimidazo[1,2-a]pyridine “A230”2-[2-(Aminocarbonylmethoxy)-4-(aminocarbonylmethoxy)-6-ethylphenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo-[1,2-a]pyridine “A231”2-[2-(Aminocarbonylmethoxy)-5-chloro-4-methoxy-6-methyl-phenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]- pyridine“A232” 2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methylphenyl]-3-(2-methyl-6-nitrophenylamino)-6-fluoroimidazo[1,2-a]- pyridine “A233”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methylphenyl]-3-(2,6-dibromophenylamino)-6-fluoroimidazo[1,2-a]pyridine “A234”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methylphenyl]-3-(2,6-dimethyl-4-fluorophenylamino)-6-fluoroimidazo- [1,2-a]pyridine“A235” 2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-ethylphenyl]-3-(2,6-dimethyl-4-fluorophenylamino)-6-fluoroimidazo[1,2-a]- pyridine“A236” 2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methylphenyl]-3-(2-methyl-6-trifluoromethylphenylamino)-6-fluoroimidazo-[1,2-a]pyridine “A237”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methylphenyl]-3-(2,6-dimethylphenylamino)-6,8-difluoroimidazo[1,2-a]- pyridine “A238”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methylphenyl]-3-(2,6-dibromo-4-fluorophenylamino)-6-fluoroimidazo- [1,2-a]pyridine“A239” 2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methylphenyl]-3-(2,6-dibromo-4-methylphenylamino)-6-fluoroimidazo- [1,2-a]pyridine“A240” 2-[2-(Aminocarbonylmethoxy)-6-ethylphenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridine “A241”2-[2-(Aminocarbonylmethoxy)-6-ethylphenyl]-3-(2,6-dichlorophenylamino)-6-fluoroimidazo[1,2-a]pyridine “A242”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methylphenyl]-3-(2-fluoro-6-trifluoromethylphenylamino)-6-fluoroimidazo-[1,2-a]pyridine “A243”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methylphenyl]-3-(2-fluoro-6-bromophenylamino)-6-fluoroimidazo[1,2-a]- pyridine “A244”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methylphenyl]-3-(2,4,6-trifluorophenylamino)-6-fluoroimidazo[1,2-a]- pyridine “A245”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-ethylphenyl]-3-(2,6-dimethyl-4-methoxycarbonylphenylamino)-6-fluoro-imidazo[1,2-a]pyridine “A246”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methylphenyl]-3-(2-methyl-6-methoxycarbonylphenylamino)-6-fluoro-imidazo[1,2-a]pyridine “A247”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-ethylphenyl]-3-(2-methyl-6-trifluoromethylphenylamino)-6-fluoroimidazo- [1,2-a]pyridine“A248” 2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methylphenyl]-3-(2-fluoro-6-chlorophenylamino)-6-fluoroimidazo[1,2-a]- pyridine “A249”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methylphenyl]-3-(2,5-dimethyl-4,6-dibromophenylamino)-6-fluoroimidazo- [1,2-a]pyridine“A250” 2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methylphenyl]-3-(2,4-dimethyl-6-nitrophenylamino)-6-fluoroimidazo[1,2-a]- pyridine“A251” 2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methylphenyl]-3-(2,6-dimethyl-4-fluorophenylamino)-6,8-difluoroimidazo-[1,2-a]pyridine “A252”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methylphenyl]-3-(2,6-difluoro-4-bromophenylamino)-6-fluoroimidazo- [1,2-a]pyridine“A253” 2-[2-(Aminocarbonylmethoxy)-6-methylphenyl]-3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridine “A254”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methylphenyl]-3-(2,6-dimethyl-4-nitrophenylamino)-6-fluoroimidazo[1,2-a]- pyridine“A255” 2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-ethylphenyl]-3-(2,6-dimethyl-4-fluorophenylamino)-6,8-difluoroimidazo- [1,2-a]pyridine“A256” 2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-methylphenyl]-3-(2-chloro-6-methylphenylamino)-6-fluoroimidazo[1,2-a]- pyridine “A257”2-[2-(Aminocarbonylmethoxy)-4-methoxy-6-ethylphenyl]-3-(2-chloro-6-methylphenylamino)-6-fluoroimidazo[1,2-a]- pyridine

and pharmaceutically usable derivatives, solvates, salts andstereoisomers thereof, including mixtures thereof in all ratios. 9.Process for the preparation of compounds of the formula I according toclaim 1 and pharmaceutically usable derivatives, solvates, salts andstereoisomers thereof, characterised in that a) a compound of theformula II

in which X, Y, R², R^(2′), R^(2″), R⁴, R^(4′) and n have the meaningsindicated in claim 1, is reacted with a compound of the formula III

in which R¹, R^(1′) and R^(1″) have the meanings indicated in claim 1,and with a compound of the formula IV

in which R, R′, R³ and R^(3′) have the meanings indicated in claim 1, orb) a compound of the formula II is reacted with a compound of theformula III and with a compound of the formula IV

in which R, R′, R³ and R^(3′) have the meanings indicated in claim 1,and/or a base or acid of the formula I is converted into one of itssalts.
 10. Medicaments comprising at least one compound of the formula Iaccording to claim 1 and/or pharmaceutically usable derivatives,solvates, salts and stereoisomers thereof, including mixtures thereof inall ratios, and optionally excipients and/or adjuvants.
 11. Medicamentscomprising at least one compound of the formula I according to claim 1and/or pharmaceutically usable derivatives, solvates and stereoisomersthereof, including mixtures thereof in all ratios, and at least onefurther medicament active ingredient.
 12. A method of using a compoundaccording to claim 1 comprising preparing a medicament for the treatmentof type 1 and type 2 diabetes with said compound.
 13. A method of usinga compound according to claim 1 comprising preparing a medicament forlowering blood sugar with said compound.
 14. A method of using acompound according to claim 1 comprising preparing a medicament for thetreatment of type 1 and type 2 diabetes with said compound and a furthermedicament active ingredient.
 15. Set (kit) consisting of separate packsof (a) an effective amount of a compound of the formula I according toclaim 1 and/or pharmaceutically usable derivatives, solvates, salts andstereoisomers thereof, including mixtures thereof in all ratios, and (b)an effective amount of a further medicament active ingredient.
 16. Amethod of using the compounds according to claim 1 and/orphysiologically acceptable salts, salts and solvates thereof whichcomprises preparing a medicament for lowering blood sugar with saidcompounds of claim 1 and/or physiologically acceptable salts thereof anda further medicament active ingredient.